3-Methoxybenzaldehyde → HCID 2692519, compound

Participants

Reaction Steps

To a solution of t-butyl carbazate (5.59 g, 42.3 mmol) in ethyl acetate (15 mL) was added with stirring m-anisaldehyde (5.17 mL, 5.76 g, 42.3 mmol). Hexanes (70 mL) was added slowly and crystallization occurred. The resulting slurry was stirred at rt for 45 min and then cooled to 0° C. The slurry was stirred at 0° C. for 60 min, then filtered and rinsed with cold hexanes (20 mL), and dried in vacuo at 40° C. to afford the title compound as a solid (9.68 g, 91.4%): mp 135.6-137.4° C.; 1H NMR (DMSO-d6) δ 10.93 (s, 1H), 7.29 (t, 1 H, J=8 Hz), 7.14 (d, 2 H, J=7 Hz), 6.92 (q, 1 H, J=7 Hz), 3.75 (s, 3 H), 1.45 (s, 9 H); 13C NMR (DMSO-d6) δ 160.2, 153.1, 143.7, 136.8, 130.5, 120.0, 116.2, 111.3, 80.1, 55.7, 28.7; IR (KBr mull) 3360, 3010, 2982, 2838, 1510, 1487 cm−1. A portion was recrystallized from ethyl acetate and submitted for elemental analysis. Anal. Calcd. for C13H18N2O3: C, 62.38; H, 7.25; N, 11.19. Found: C, 62.34.; H, 7.46; N, 11.19.

Provenance & Evidence