Method for the preparation of 4-phenyl-1,3-benzodiazepins and pr

Details Method for the preparation of 4-phenyl-1,3-benzodiazepins and pr Method for the preparation of 4-phenyl-1,3-benzodiazepins and pr

1992-11-23

1994-09-20

Hollrah, Glennon H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

564221, 564272, C07C23108

Patent

active

053490860

ABSTRACT:
A compound of the formula ##STR1## is prepared by reacting an N-acylated-o-toluidine of the formula ##STR2## with n-alkyllithium to form a dilithio intermediate of the formula ##STR3## which can then be quenched with N-benzylidenemethylamine to form compound II. Hydrolysis of compound(II) yields the free base ##STR4## or its salt, which can be cyclized to form 4,5-dihydro-2,3-dimethyl-4-phenyl-3H-1,3-benzodiazepine or its physiologically acceptable salts, which are useful as pharmacological agents.

REFERENCES:
Muchowski et al., "Ortho Functionalization of N-(t-butoxycarbonyl) aniline, "J. O. C. 45:4798-4801. (1980).
Fuhrer et al. "Ortho Functionalization of Aromatic Amines: Ortho lithiation of N-Picloylanines", J. O. C. 44:1133-1136 (1979).
Muchowski et al. "O-Functionalization of Aromatic Amines: O-Lithiatian of N-Pivaloylanilines," JOC 44:1133-36 (1979).

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