Sodium Hydroxide → HCID 57748288, compound

Participants

Reaction Steps

Methyl 4-aminocarbonyl-5-(pentan-3-ylamino)-2-(trifluoromethyl)benzoate (0.818 mmol) was dissolved in methanol (2 mL) and was treated with 2M sodium hydroxide (1 mL, 2 mmol) at 45° C. for 1.5 h. The reaction mixture was cooled to ambient temperature and was concentrated to afford an aqueous residue that was washed with ether, then cooled in an ice bath and acidified with 1N hydrochloric acid to pH ˜3. The precipitate was collected by filtration, washed with water, then dried to afford 4-aminocarbonyl-5-(pentan-3-ylamino)-2-(trifluoromethyl)benzoic acid (233 mg, 0.733 mmol, 90% yield over 2 steps). 1H NMR (400 MHz, d6-DMSO): δ 13.5 (br s, 1H), 8.74 (d, 1H), 8.21 (br s, 1H), 7.95 (s, 1H), 7.46 (br s, 1H), 6.94 (s, 1H), 3.51-3.43 (m, 1H), 1.63-1.51 (m, 2H), 1.51-1.39 (m, 2H), 0.87 (t, 6H); MS (EI) for C14H17F3N2O3: 319 (MH+).

Provenance & Evidence