Formic Acid → HCID 86634878, compound

Participants

Reaction Conditions

Reaction Steps

Formic acid (0.35 mL, 9.1 mmol) was added to acetic anhydride (0.69 mL, 7.3 mmol) at 0° C. The mixture was warmed to 60° C. for 2 hours, then cooled to 0° C. To the anhydride mixture was added a solution of methyl 2-(4-aminophenyl)acetate (0.95 g, 5.7 mmol) in tetrahydrofuran (14 mL). The mixture was warmed to room temperature and stirred for 18 hours. The reaction mixture was neutralized with saturated aqueous sodium bicarbonate and diluted with ether. The ether layer was separated, dried over sodium sulfate, and concentrated. The residue was filtered through silica (1% methanol/dichloromethane eluent) to give methyl 2-(4-formamidophenyl)acetate (0.8 g, 4.14 mmol, 56% yield). The product was dissolved in tetrahydrofuran (14 mL) and cooled to 0° C. Borane methyl sulfide complex (0.393 mL, 4.14 mmol) was added. After 15 minutes, the mixture was warmed to room temperature for 30 minutes. The mixture was cooled to 0° C. again, and 5 mL of methanol was added. The mixture was concentrated and the residue was purified by silica chromatography (10% ethyl acetate/hexane eluent) to give methyl 2-(4-(methylamino) phenyl)acetate: 1H NMR (300 MHz, CDCl3) δ ppm 2.82 (s, 3H), 3.51 (s, 2H), 3.67 (s, 3H), 6.51-6.61 (m, 2H), 6.99-7.15 (m, 2H); MS (ESI+) m/z 179.9 (M+H)+.

Provenance & Evidence