Ammonia → HCID 178422924, compound

Participants

Reaction Steps

Concentrated sulfuric acid (18 M; 11.0 mL) was added to 2,2-dimethoxy-N-(4-methylbenzyl)-acetamide (1.95 g, 8.73 mmol) at ambient temperature, and the solution was stirred overnight at ambient temperature. The reaction mixture was added to ≈100 mL of ice, and the pH of the mixture was adjusted to ≈5 with concentrated aq. NH3 solution. The yellow precipitate was filtered off, washed with water, and dried in vacuo overnight to give the title compound as yellow solid. It was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6): δ=8.79 (s, 1H), 7.81 (d, J=8.4 Hz, 1H), 7.44 (s, 1H), 7.14 (dd, J=1.6, 8.4 Hz, 1H), 6.76 (s, 1H), 2.42 (s, 3H); —OH not apparent. MS(ES+): m/z=160.25 (100) [MH+], 142.13 (12) [MH+—H2O]. HPLC: tR=2.15 min (polar—5 min, ZQ2), 2.25 min (polar—5 min, ZQ3).

Provenance & Evidence