Process for the preparation of 5-fluoroanthranilic alkyl esters

Details Process for the preparation of 5-fluoroanthranilic alkyl esters Process for the preparation of 5-fluoroanthranilic alkyl esters

1994-10-06

1996-08-06

Dees, Jos e G.

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

Organic compounds

Carboxylic acid esters

560 47, 560103, 562433, 562456, 562458, 562493, C07C22952, C07C 6976, C07C 6304

Patent

active

055435505

ABSTRACT:
The present invention relates to a process for the preparation of 5-fluoroanthranilic alkyl esters and/or 5-fluoroanthranilic acid, which comprises dissolving a 3-fluorobenzoic alkyl ester in sulfuric acid and reacting the solution with a nitrating acid at from -10.degree. to 30.degree. C., then adding water, separating off the nitrated reaction product and reacting it with hydrogen at from 50.degree. to 120.degree. C. under elevated pressure in the presence of a catalyst comprising a metal of the platinum group and sulfur, and, if desired, removing 5-fluoroanthranilic alkyl esters by distillation and hydrolyzing them to give 5-fluoroanthranilic acid.

REFERENCES:
patent: 4059627 (1977-11-01), Kritzler et al.
patent: 4506089 (1985-03-01), Hackenberger et al.
Journal of the American Chemical Society, The Synthesis of Some Alkyl and Dialkylaminoalkyl Esters of 2-Nitro-5-fluorobenzoic Acid and 2-Amino-fluorobenzoic Acid, Bd. 66, Jul. 1944, pp. 1165-1166.
Tetrahedron Letters, Synthesis and DNA Crosslinking Ability of a Dimeric Anthramycin Analog, Bd. 29, Nr. 40, 1988, pp. 5105-5108.

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