Process for the preparation of N-(4-hydroxyphenyl)-retinamide

Details Process for the preparation of N-(4-hydroxyphenyl)-retinamide Process for the preparation of N-(4-hydroxyphenyl)-retinamide

1993-07-20

1995-03-21

Kumar, Shailendra

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

Organic compounds

Amino nitrogen containing

556410, 564182, 564184, C07C23102

Patent

active

053997573

ABSTRACT:
This invention is directed to an efficient, mild, high yield process for the large scale synthesis of N-(4-hydroxyphenyl)-retinamide comprising the preferred steps of reacting retinoic acid with dimethylchloroformamidinium chloride to from retinoyl chloride which in turn is reacted with bis-(N,O)-trimethylsilyl-p-aminophenol to eventually form N-(4-hydroxyphenyl)-retinamide and to the novel use of bis-(N,O)-trimethylsilyl-p-aminophenol to eventually form a hydroxyphenylamide, particularly N-(4-hydroxyphenylretinamide and methods of recrystallizing N-(4-hydroxyphenyl)-retinamide to obtain the stable "A" polymorph thereof.

REFERENCES:
patent: 4468395 (1984-08-01), Vorbrugen et al.
patent: 4743400 (1988-05-01), Maryanoff
Burgert et al., Chem. Ber. 120, 691-694, 1987.

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