Anthranilic Acid → (2-Aminophenyl)(pyrrolidin-1-yl)methanone

Participants

Reaction Steps

To a solution of 2-aminobenzoic acid (5.0 g, 36.5 mol) in tetrahydrofuran (50 mL) was added N,N′-carbonyldiimidazole (6.5 g, 40.1 mol) at 25° C., the resulting mixture was stirred for 1 hour at this temperature. Then pyrrolidine (3.5 g, 40.1 mmol) was added and the mixture was stirred overnight. The solvent was removed under the reduced pressure and the residue was washed with water and extracted with dichloromethane, the organic phase was dried over anhydrous sodium sulfate, concentrated to afford the product (2-aminophenyl)(pyrrolidin-1-yl)methanone (5.4 g, yield 66%), which was used for the next step without further purification. 1H NMR (400 MHz, CDCl3) δ ppm 7.12-7.21 (m, 2H), 6.66-6.71 (m, 2H), 4.62 (br s, 2H), 3.63 (br s, 2H), 3.47 (br s, 2H), 1.87-1.94 (m, 4H).

Provenance & Evidence