A Simple and Efficient Synthesis of 2-(N-Phenylamino)- Benzoic Acids

Abstract

A new method for the synthesis of 2-(N-phenylamino)benzoic acids is presented, with 2-fluorobenzoic acids and anilines as starting materials. Several experimental conditions as well as the factors influencing the outcome of the reaction are described.

Utilization of Lithium Amide in the Synthesis of N-Arylanthranilic Acids and N-Arylanthranilamides

“…Triarylbismuth reagents have also been successfully employed in the preparation of N -arylanthranilates as well as other diarylamines . A catalyst-free substitution of 2-fluorobenzoic acids with lithium anilides prepared from the corresponding anilines and lithium hexamethyldisilazide at −78 °C has been demonstrated . While this catalyst-free methodology was very attractive, the cryogenic reaction conditions and large quantities of waste complicate the scale-up of such a process.…”

“…We investigated the use of the strong base LDA to promote the reaction of 2-chloro-4-iodoaniline ( 1a ) with 2,3,4-trifluorobenzoic acid ( 2a ). It was found that by adding portions of LDA while the reaction was less than −20 °C and warming the reaction mixture to room temperature between additions, the reaction proceeded in high yield 8c…”