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Abstract:

In the acid hydrolysis of diazepam (1), several unusual products, apart from 2‐(N‐methylamino)‐5‐chlorobenzophenone (2) and glycine, were isolated. On the assumption that some of those products could arise from further degradation of 2, the reaction of this compound with 0.5–2 M HCl was studied, in 1:1 MeOH—H2O, at 60 and 80 °C. Several unexpected products were isolated from the reaction of 2 with HCl, namely, 2‐amino‐5‐chlorobenzophenone (3), 2‐(N,N‐dimethylamino)‐5‐chlorobenzophenone (4), 2‐(N‐methylamino)‐3,5‐dichlorobenzophenone (5), 2‐amino‐3,5‐dichlorobenzophenone (6), 2, 4‐dichloro‐10‐methyl‐9,10‐acridinone (7), and 2, 4‐dichloro‐9, 10‐acridinone (8). The methyl transfers, the chlorination, and the cyclization reactions that give rise to products 3–8 are unexpected under the present reaction conditions. The rate of reaction of 2, as well as the rate of formation of compounds 3–6, was measured at several HCl concentrations. Copyright © 1995 Wiley‐Liss, Inc., A Wiley Company

Registro:

Documento: Artículo
Título:Acid hydrolysis of diazepam. Kinetic study of the reactions of 2‐(N‐methylamino)‐5‐chlorobenzophenone, with HCl in MeOHH2O
Autor:Nudelman, N.S.; de Waisbaum, R.G.
Filiación:Depto. de Quimica Organica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pab. II, P.3, Ciudad Universitaria, Buenos Aires, 1428, Argentina
Palabras clave:5 chloro 2 (methylamino)benzophenone; benzophenone derivative; diazepam; unclassified drug; article; chemical reaction; drug degradation; drug determination; drug hydrolysis; drug structure; Acids; Benzophenones; Chromatography, Gas; Computer Simulation; Diazepam; Hydrolysis; Kinetics; Methanol; Models, Chemical; Spectrophotometry, Ultraviolet; Support, Non-U.S. Gov't
Año:1995
Volumen:84
Número:8
Página de inicio:998
Página de fin:1004
DOI: http://dx.doi.org/10.1002/jps.2600840817
Título revista:Journal of Pharmaceutical Sciences
Título revista abreviado:J. Pharm. Sci.
ISSN:00223549
CAS:2-methylamino-5-chlorobenzophenone, 1022-13-5; Acids; Benzophenones; Diazepam, 439-14-5; Methanol, 67-56-1
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223549_v84_n8_p998_Nudelman

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Citas:

---------- APA ----------
Nudelman, N.S. & de Waisbaum, R.G. (1995) . Acid hydrolysis of diazepam. Kinetic study of the reactions of 2‐(N‐methylamino)‐5‐chlorobenzophenone, with HCl in MeOHH2O. Journal of Pharmaceutical Sciences, 84(8), 998-1004.
http://dx.doi.org/10.1002/jps.2600840817
---------- CHICAGO ----------
Nudelman, N.S., de Waisbaum, R.G. "Acid hydrolysis of diazepam. Kinetic study of the reactions of 2‐(N‐methylamino)‐5‐chlorobenzophenone, with HCl in MeOHH2O" . Journal of Pharmaceutical Sciences 84, no. 8 (1995) : 998-1004.
http://dx.doi.org/10.1002/jps.2600840817
---------- MLA ----------
Nudelman, N.S., de Waisbaum, R.G. "Acid hydrolysis of diazepam. Kinetic study of the reactions of 2‐(N‐methylamino)‐5‐chlorobenzophenone, with HCl in MeOHH2O" . Journal of Pharmaceutical Sciences, vol. 84, no. 8, 1995, pp. 998-1004.
http://dx.doi.org/10.1002/jps.2600840817
---------- VANCOUVER ----------
Nudelman, N.S., de Waisbaum, R.G. Acid hydrolysis of diazepam. Kinetic study of the reactions of 2‐(N‐methylamino)‐5‐chlorobenzophenone, with HCl in MeOHH2O. J. Pharm. Sci. 1995;84(8):998-1004.
http://dx.doi.org/10.1002/jps.2600840817