Formaldehyde → HCID 11817219, compound

Participants

Reaction Steps

To a round bottomed flask containing 3-acetamidophenol (5 g) in ethanol (20 ml) was added diethylamine (2.6 g) and formaldehyde (1.1 g). The resulting mixture was stirred at reflux for 24 hours. After this time, the solvent was evaporated and the residue was purified by column chromatography (silica, dichloromethane/methanol 80:20) to give N-(4-Diethylaminomethyl-3-hydroxy-phenyl)-acetamide (4.1 g, 53%). 1H NMR (250 MHz, CDCl3) δH: 7.05 (1H, d, J=8.2), 6.89 (1H, d, J=8.2), 6.80 (1H, s), 3.70 (2H, s), 2.60 (2H, q, J=7.2), 2.12 (3H, s, NHCOCH3), 1.10 (3H, t, J=7.2). IR (NEAT) CM−1; 3500-2800 (broad-OH band), 1668, 1614, 1538, 1454, 1386, 1273, 1194, 1166, 1114, 1032, 863, 773 and 736.ACCURATE MASS: 237.16042 gmol−1 (C13H21O2N2 requires 237.16029); ELEMENTAL ANALYSIS; C, 64.07; H, 8.62; N, 10.88; (calc values; C, 65.67; H, 8.53; N, 11.86). MS; molecular ion peak at m/z=237

Provenance & Evidence