Preparation of alpha-chloroacetoacetanilide compounds

Details Preparation of alpha-chloroacetoacetanilide compounds Preparation of alpha-chloroacetoacetanilide compounds

1994-06-15

1995-08-15

Reamer, James H.

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

Organic compounds

Amino nitrogen containing

C07C22522

Patent

active

054421152

ABSTRACT:
A process for the preparation of .alpha.-chloroacetoacetanilide compounds (.alpha.-Cl AAA) which comprises the steps of:
(a) reacting an acetoacetanilide compound (AAA) with chlorine in the presence of a solvent mixture consisting essentially of an organic solvent and water, wherein the percent water to organic solvent in the solvent mixture is between about 10% and 150% (v/v);
(b) isolating the .alpha.-Cl AAA produced in step (a); and
(c) optionally hydrogenating any .alpha.,.alpha.-dichloroacetoacetanilide compound (.alpha.,.alpha.-diCl AAA) produced in step (a), with hydrogen in the presence of a catalyst selected from the group consisting of palladium, platinum and Raney nickel, and in the presence of a solvent mixture consisting essentially of water and an organic solvent, wherein the percent of the water to the organic solvent in the solvent mixture is between 10% to 150% (v/v), for a period of time sufficient to produce .alpha.-Cl AAA; and isolating the .alpha.-Cl AAA so produced.
The present invention also relates to a process for the dechlorination of .alpha.,.alpha.-diCl AAA wherein the .alpha.,.alpha.-diCl AAA is hydrogenated with hydrogen in the presence a catalyst selected from the group consisting of palladium, platinum and Raney nickel, and in the presence of a solvent mixture consisting essentially of water and an organic solvent, wherein the percent of the water to the organic solvent in the solvent mixture is between 10% to 150% (v/v), for a period of time sufficient to produce either .alpha.-Cl AAA or AAA.

REFERENCES:
patent: 3459801 (1969-08-01), Beriger
patent: 5049698 (1991-09-01), Newland

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