Ammonia → HCID 59442088, compound

Participants

Reaction Steps

To a solution of 2-amino-5,6-difluoro benzoic acid (3.78 g, 21.8 mmol) in tetrahydrofuran (500 mL) was added EDCl.HCl (8.5 g, 44.0 mmol, 2.0 equiv.), HOBT (5.9 g, 44 mmol, 2.0 equiv.) and ammonia as a 0.5M solution in dioxanes (218 mL, 109 mmol, 5 equiv.). The resultant slurry was stirred for 24 hours, and then solids removed by filtration through celite. The filtrate was taken to a residue under reduced pressure and partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate, filtered, taken to a residue under reduced pressure, and purified by chromatography on SiO2 (Ethyl acetate/Hexanes) to afford analytically pure 2-amino-5,6-difluorobenzamide as a white crystalline solid (2.73 g, 15.8 mmol, 72% Yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 5.78 (s, 2 H), 6.45 (ddd, J=9.16, 4.03, 1.83 Hz, 1 H), 7.10-7.18 (m, 1 H), 7.69 (d, J=11.00 Hz, 2 H).

Provenance & Evidence