This document describes an efficient two-step synthesis of the drug Atenolol using microwave dielectric heating. In the first step, p-hydroxyphenylacetamide is reacted with epichlorohydrin under microwave conditions to form an epoxy derivative in 70% yield. In the second step, the epoxy derivative is reacted with isopropyl amine and water under microwave heating to form Atenolol in 93% yield. Overall, this microwave-assisted synthesis provides Atenolol in 65% yield from the starting material, which is faster and higher yielding than conventional heating methods.
Research Inventy : International Journal of Engineering and Scienceresearchinventy
Research Inventy : International Journal of Engineering and Science is published by the group of young academic and industrial researchers with 12 Issues per year. It is an online as well as print version open access journal that provides rapid publication (monthly) of articles in all areas of the subject such as: civil, mechanical, chemical, electronic and computer engineering as well as production and information technology. The Journal welcomes the submission of manuscripts that meet the general criteria of significance and scientific excellence. Papers will be published by rapid process within 20 days after acceptance and peer review process takes only 7 days. All articles published in Research Inventy will be peer-reviewed.
Synthesis, Reactions resonance, Reactivity and uses of naphthalene, Anthracene, Phenanthrene, naphthol, Anthraquinone and phenanthroquinone, diphenyl methane and triphenyl methane
Research Inventy : International Journal of Engineering and Scienceresearchinventy
Research Inventy : International Journal of Engineering and Science is published by the group of young academic and industrial researchers with 12 Issues per year. It is an online as well as print version open access journal that provides rapid publication (monthly) of articles in all areas of the subject such as: civil, mechanical, chemical, electronic and computer engineering as well as production and information technology. The Journal welcomes the submission of manuscripts that meet the general criteria of significance and scientific excellence. Papers will be published by rapid process within 20 days after acceptance and peer review process takes only 7 days. All articles published in Research Inventy will be peer-reviewed.
Synthesis, Reactions resonance, Reactivity and uses of naphthalene, Anthracene, Phenanthrene, naphthol, Anthraquinone and phenanthroquinone, diphenyl methane and triphenyl methane
Synthesis and Characterization of New Complexes of 2-(6-Methoxybenzo[d]thiazo...IOSR Journals
Abstract: The synthesis and characterization of manganese (ІІ), cobalt (ІІ), nickel (ІІ), copper (ІІ), zinc (ІІ), cadmium (ІІ) and mercury (ІІ) bidentate 2-(6-methoxybenzo[d]thiazol-2-ylamino)-2-phenyl acetonitrile ligand which was prepared from Benz aldehyde and 6-methoxybenzo[d]thiazol-2-amine in the presence of KCN and acidic medium. The complexes were synthesized by treating an ethanolic solution of the ligand with appropriate amount of metal salts [1:2] [M: L] ratio. The complexes were characterized by using metal and elemental chemical analysis, molar conductance, magnetic susceptibility measurements, FTIR , electronic spectral and mole ratio method. According to the obtained data the probable coordination geometries of manganese (ІІ), cobalt (ІІ), nickel (ІІ), copper (ІІ) zinc (ІІ), cadmium (ІІ) and mercury (ІІ) in these complexes are octahedral. All complexes were found to be non-electrolyte in absolute ethanol, and the complexes were formulated as [ML2Cl2] XH2O. Keywords: 2-(6-methoxybenzo[d]thiazol-2-ylamino)-2-phenyl acetonitrile, N2-donor, transition metals.
Removal of Coke during Steam Reforming of Ethanol over La-CoOx Catalystinventy
Research Inventy : International Journal of Engineering and Science is published by the group of young academic and industrial researchers with 12 Issues per year. It is an online as well as print version open access journal that provides rapid publication (monthly) of articles in all areas of the subject such as: civil, mechanical, chemical, electronic and computer engineering as well as production and information technology. The Journal welcomes the submission of manuscripts that meet the general criteria of significance and scientific excellence. Papers will be published by rapid process within 20 days after acceptance and peer review process takes only 7 days. All articles published in Research Inventy will be peer-reviewed.
IJERA (International journal of Engineering Research and Applications) is International online, ... peer reviewed journal. For more detail or submit your article, please visit www.ijera.com
IJERA (International journal of Engineering Research and Applications) is International online, ... peer reviewed journal. For more detail or submit your article, please visit www.ijera.com
Organic chemistry has two main divisions. One division deals with aliphatic (fatty) compounds, the first compounds you encountered in Organic Chemistry I. The second division includes the aromatic (fragrant) compounds, of which benzene is a typical example
Purines are the cyclic diureides, consisting of a pyrimidine ring fused with an imidazole ring. Purine m.p. 212-213⁰C is a synthetic compound. Purine is not found naturally, but it’s derivatives, adenine, and guanine are found in nature. These are the building blocks of nucleic acid RNA and DNA. Purine can exist in four tautomeric forms in which the hydrogen atom is attached to the different nitrogen atom, N-1, N-3, N-7, and N-9. Purines are a type of chemical compound found in foods and drinks that are part of a normal diet. A small number of foods contain concentrated levels of purines, such as seafood, organ meats, and alcoholic beverages, especially beer.
Synthesis and Characterization of New Complexes of 2-(6-Methoxybenzo[d]thiazo...IOSR Journals
Abstract: The synthesis and characterization of manganese (ІІ), cobalt (ІІ), nickel (ІІ), copper (ІІ), zinc (ІІ), cadmium (ІІ) and mercury (ІІ) bidentate 2-(6-methoxybenzo[d]thiazol-2-ylamino)-2-phenyl acetonitrile ligand which was prepared from Benz aldehyde and 6-methoxybenzo[d]thiazol-2-amine in the presence of KCN and acidic medium. The complexes were synthesized by treating an ethanolic solution of the ligand with appropriate amount of metal salts [1:2] [M: L] ratio. The complexes were characterized by using metal and elemental chemical analysis, molar conductance, magnetic susceptibility measurements, FTIR , electronic spectral and mole ratio method. According to the obtained data the probable coordination geometries of manganese (ІІ), cobalt (ІІ), nickel (ІІ), copper (ІІ) zinc (ІІ), cadmium (ІІ) and mercury (ІІ) in these complexes are octahedral. All complexes were found to be non-electrolyte in absolute ethanol, and the complexes were formulated as [ML2Cl2] XH2O. Keywords: 2-(6-methoxybenzo[d]thiazol-2-ylamino)-2-phenyl acetonitrile, N2-donor, transition metals.
Removal of Coke during Steam Reforming of Ethanol over La-CoOx Catalystinventy
Research Inventy : International Journal of Engineering and Science is published by the group of young academic and industrial researchers with 12 Issues per year. It is an online as well as print version open access journal that provides rapid publication (monthly) of articles in all areas of the subject such as: civil, mechanical, chemical, electronic and computer engineering as well as production and information technology. The Journal welcomes the submission of manuscripts that meet the general criteria of significance and scientific excellence. Papers will be published by rapid process within 20 days after acceptance and peer review process takes only 7 days. All articles published in Research Inventy will be peer-reviewed.
IJERA (International journal of Engineering Research and Applications) is International online, ... peer reviewed journal. For more detail or submit your article, please visit www.ijera.com
IJERA (International journal of Engineering Research and Applications) is International online, ... peer reviewed journal. For more detail or submit your article, please visit www.ijera.com
Organic chemistry has two main divisions. One division deals with aliphatic (fatty) compounds, the first compounds you encountered in Organic Chemistry I. The second division includes the aromatic (fragrant) compounds, of which benzene is a typical example
Purines are the cyclic diureides, consisting of a pyrimidine ring fused with an imidazole ring. Purine m.p. 212-213⁰C is a synthetic compound. Purine is not found naturally, but it’s derivatives, adenine, and guanine are found in nature. These are the building blocks of nucleic acid RNA and DNA. Purine can exist in four tautomeric forms in which the hydrogen atom is attached to the different nitrogen atom, N-1, N-3, N-7, and N-9. Purines are a type of chemical compound found in foods and drinks that are part of a normal diet. A small number of foods contain concentrated levels of purines, such as seafood, organ meats, and alcoholic beverages, especially beer.
Studies on Nitration of Phenol over Solid Acid Catalyst | Crimson PublishersDanesBlake
Phenol was selectively nitrated in liquid phase to produce ortho-nitrophenol using dilute nitric acid (30%) at room temperature in presence of hydrochloric acid treated γ-alumina. Initially Al(NO3) and NH4HCO3 were reacted to prepare Al (OH)3 which on successive calcinations at 550 ᴼC for 5h produce γ-alumina. The γ-alumina was characterized by BET, XRD, SEM and NH3-TPD analysis. The XRD profile confirmed the crystalline structure of the solid acid catalyst γ-alumina. The NH3-TPD analysis showed the development of lewis acidity on the surface of hydrochloric acid treated γ-alumina. The effects of various parameters such as concentration of reactants, types of catalyst, weight of the catalyst, solvent, temperature and time of reaction have been studied. The kinetics of the reaction was also investigated.
Reaction of aniline with ammonium persulphate and concentrated hydrochloric a...Maciej Przybyłek
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Studies on Nitration of Phenol over Solid Acid Catalyst by Lipika Das, Koushi...crimsonpublisherspps
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https://crimsonpublishers.com/pps/fulltext/PPS.000505.php
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1. A new approach to the synthesis of Atenolol
using Coherent Synthesis™™
This report describes the efficient two-step synthesis of
Atenolol from p-hydroxyphenylacetamide, using microwave
dielectric heating. In both steps, significant acceleration of
reaction rates and a slight increase in the yield were achieved
compared to conventional procedures.
O
1) a) Cl
O
H2N O
b) BnNMe3Cl
OH H2N
O OH
2)
a) H N H
2
N
b) H2O Atenolol
INTRODUCTION
Atenolol (2-[4-[2-hydroxy- period of time. In this report, we
Coherent Synthesis™ Application Note
(isopropylamino)propoxy]phenyl] describe a versatile new approach for
acetamide) is a β1-selective the synthesis of Atenolol employing
(cardioselective) adrenoreceptor Coherent Synthesis™ technology
blocking agent that is used for based on microwave dielectric heating.
treatment of hypertension and angina. The use of microwave dielectric
Atenolol, in a formulation containing heating as an efficient tool for en-
the racemic mixture, was one of the hancing reaction rates, especially for
top-selling drugs in the US market in transformations that require long
the year 2000.1 periods of time and high temperatures,
The most straightforward method of has been well described.4 It is
preparing Atenolol involves the suggested that the synthesis of
reaction of commercially available 4- Atenolol in the solution phase under
hydroxyphenylacetamide (1) with microwave conditions would provide a
epichlorohidrin, followed by the speedy source not only of this
addition of isopropylamine2,3 at important drug but also of a library of
elevated temperatures for a long its analogues.
2. EXPERIMENTAL PROCEDURE Step 2
Step 1 Preparation of Atenolol (4):
Preparation of 1-[p-(carbamoyl- A process vial was loaded with
methyl)phenoxy]-2,3-epoxy- isopropyl amine (6) (2.3 mL), water (0.2
propane (2): mL) and 2 (207 mg, 1.0 mmol). The
A process vial was charged with mixture was heated for 600 sec. at
epichlorohydrin (5) (2.5 mL), 130oC. After cooling, solvents were
4-hydroxyphenylacetamide,1, (302 mg, evaporated and the residue was
2.0 mmol) and benzyltrimethyl- dissolved in 1 mL of 2N HCl and filtered.
ammonium chloride (13.0 mg, 0.07 The pH of the filtrate was adjusted to
mmol). The resulting mixture was 11—12 using 30% NaOH solution. The
heated for 300 sec. at 180oC. After resulting suspension was cooled to 5oC,
cooling, the precipitate was filtered off. the precipitate was filtered and washed
The crude products 2 and 3 were with a small amount of cold water. After
separated by recrystallization from drying, 250 mg (93% yield) of Atenolol
MeOH to give 2 in 70% yield (287 mg), was obtained. mp:148-149oC, Rf=0.09
mp: 166-167oC, Rf=0.55, CHCl3/MeOH CHCl3/MeOH (5/1).
(5/1).
O
O
H2N
O 2
OH Step 1 Step 2 O OH
H2N + H2N H
O O O N
1
Cl 4
O OH H2N
5
H2N 6
O 3 Cl
Coherent Synthesis™ Conventional 2 Conventional 3
Step 1
Temp/°C 180 95 – 100 90
Time 5 min 6h 3h
Step 2 Temp/°C 130 110 40
Time 10 min 12 h 2h
Total Yield 65% NA 62%
3. RESULTS to the epoxy derivative (2) under
After investigating the procedures microwave conditions at 130oC for 600
described in the literature2,3 under sec. resulted in 93% isolated yield of
microwave conditions, it was found Atenolol. The presence of water as
that benzyltrimethylammonium co-solvent is essential to improve the
chloride was a better catalyst than yield of the product (98% vs. 83%
morpholine or piperidine for synthesis HPLC yields). The total yield of
of the epoxy derivative (2). A high Atenolol from the amide (1) was 65%.
temperature and a relatively short
reaction time is necessary (180oC, 300
sec.) to reach complete conversion of CONCLUSIONS
the initial amide (1) with this catalyst An efficient, 2-step synthesis of
under microwave irradiation. Upon Atenolol from p-hydroxyphenylacetamide
work up and recrystallisation from was carried out in a SmithSynthesizer™.
methanol, the epoxide (2) was In both steps, significant acceleration
obtained with a 70% yield. According of the reaction rate were achieved
to literature2,3, Atenolol can be compared with the rates achieved
produced from the epoxy derivative using conventional literature
(2) and chloride (3), with an excess of procedures. The present approch can
isopropyl amine at an elevated be applied for general use, since the
temperature and pressure. However, reaction of phenols with epichlorohidrin
when the conditions described by S.M. and the subsequent treatment with
Jang et al.3 amines can be applied not only to the
(40-60oC/1–2 h) were tried in our synthesis of Atenolol but also to the
laboratories, conversion of reagent 2 preparation of other α-amino alcohol
resulted in a low yield of Atenolol based drugs, such as Propranolol,
(62%). In fact, from our experience, it Metoprolol, Propafenon and their
requires a 12-hour reaction at 50oC derivatives.
(conventionally) for full conversion of 2
to Atenolol.
The addition of isopropyl amine (6)
OH O O N
O N
O H
OH H OH H
O N
Propranolol Metoprolol Propafenon
4. REFERENCES
1. http://www.rxlist.com/ Personal Chemistry AB
top200.htm. Source: Hamnesplanaden 5
Scott-Levin, Newton PA - SE-753 19 Uppsala, Sweden
Based on more than 2.04 Phone:+46(0) 18 489 9000
billion prescriptions Fax: +46(0) 18 489 9200
Coherent Synthesis™ Application Note
dispenses in US.
2. Barrett, A. M et al., US Personal Chemistry Inc.
2 Hampshire Street, Suite 100
patent US 3,934,032, 20
Foxboro, MA 02035 USA
Jan 1976. Phone: +1(508) 698 8723
Barrett, A. M et al., US Fax: +1(508) 698 9623
patent US 3,836,671, 17
September 1974. Personal Chemistry GmbH
3. Jang, S. M. et al., US Gottlieb-Daimler-Strasse 5
Patent US 5,290,958, 1 D-78467 Konstanz, Germany
March 1994. Phone: +49(0) 7531-9423460
Fax: +49(0) 7531-9423470
4. Lidström, P., Tierney, J.,
Wathey, B. and Westman,
J. Tetrahedron, 2001, 57, Personal Chemistry Limited
9225-9283. Lincoln House
The Paddocks
347 Cherry Hinton Road
Coherent SynthesisTM is an Cambridge, CB1 8DH, UK
integrated approach to Phone:+44(0) 126 025 3649
Fax: +44(0) 796 759 5278
chemical synthesis,
combining the benefits of e-mail:
fast synthesis with info@personalchemistry.com
advanced lab automation, www.personalchemistry.com
knowledge-based systems
and convenience products. Article No. 353 276