Process for producing N-acyl-acyloxy aromatic amines

Details Process for producing N-acyl-acyloxy aromatic amines Process for producing N-acyl-acyloxy aromatic amines

1984-07-03

1986-02-04

Trousof, Natalie

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

Organic compounds

Carboxylic acid esters

260404, 260463, 560 9, 560 10, 560 24, 560 27, 560 28, 560 30, 560 33, 560139, 560141, 564223, C07C10346, C07C10366, C07C125065, C07C10338

Patent

active

045687633

ABSTRACT:
N-acyl-acyloxy aromatic amines, e.g. 4-acetoxyacetanilide (AAA), are prepared by reacting a hydroxy aromatic ketone, e.g. 4-hydroxyacetophenone, with hydroxylamine or a hydroxylamine salt and a base to obtain the ketoxime of the ketone, e.g. 4-hydroxyacetophenone oxime, and then subjecting the ketoxime to a Beckmann rearrangement and accompanying acylation by contacting the ketoxime with a carboxylic acid anhydride and a Beckmann rearrangement catalyst to form the N-acyl-acyloxy aromatic amine.

REFERENCES:
patent: 2833825 (1978-05-01), Lewis
patent: 4524217 (1985-06-01), Davenport et al.
J. Pharmaceutical Sciences, vol. 59, No. 12, pp. 1738-1741; Rattie et al.
Fieser and Fieser, Organic Chemistry, 3rd Ed., Reinhold Publ. Corp., New York, 1956, pp. 211-212, 627.
Simons et al, J. Amer. Chem. Soc., 62, 485 and 486 (1940).
Dann and Mylius, Annalen der Chemie, 587 Band, 1-15, (W. Germany, 1954)-English translation provided.
Simons et al, J. Amer. Chem. Soc., 61, 1795 and 1796 (1939).
Auwers et al, Chemishe Berichte, 58, 36-51 (Germany 1925)-English translation provided.
Ganboa et al, Synthetic Communications, 13 (11) 941-944 (1983).
Pearson et al, J. Amer. Chem. Soc., 75, 5905-5908 (1953).

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