Acetone → HCID 6110721, compound

Participants

Reaction Steps

A mixture of p-acetamidobenzaldehyde (8.15 g, 50 mmol) dissolved in 200 mL of hot EtOH) and acetone (1.8 mL, 25 mmol) was added dropwise to a solution of aq. NaOH solution (2 N, 25 mL) in EtOH (150 mL). The reaction mixture was stirred for 4 h at ambient temperature and the resulting orange precipitate was filtered, washed with water and dried in vacuo to afford NW270 as a bright yellow solid (4.6 g, 53%). mp: 253-255° C. 1H NMR (250 MHz, DMSO-d6) δ (ppm): 10.18 (s, 2H, NH), 7.81-7.58 (m, 10H, HAr, Hvin), 7.22 (d, 3J=16.0 Hz, 2H, Hvin), 2.08 (s, 6H, CH3). 13C NMR (75 MHz, DMSO-d6) δ (ppm): 188.2 (C), 168.6 (C), 142.1 (CH), 141.4 (C), 129.4 (CH), 124.1 (CH), 118.9 (CH), 24.1 (CH3). MS (EI) m/z: 348.2 (M+). Anal. calcd for C21H20N2O3: C, 72.40; H, 5.79; N, 8.04. Found: C, 72.14; H, 5.78; N, 7.97%.

Provenance & Evidence