Hydrochloric Acid → HCID 326819, compound

Participants

Reaction Steps

Referring to FIG. 21, a mixture of N,N-dimethyl-meta-phenylene-diamine (800 mg, 3.8 mmol) and 6 N HCl (12 mL) was stirred at reflux. Crotonaldehyde (0.31 mL, 3.8 mmol) dissolved in toluene (1 mL) was added dropwise to the purple solution. The reaction mixture was stirred for 2 h, cooled and neutralized with solid NaOH, and extracted with toluene, then chloroform (×5). The extracts were combined, dried over Na2SO4 and evaporated to dryness. The residue was purified by column chromatography (EtOAc) to obtain 13a (304.3 mg, 1.6 mmol, 43% yield): 1H NMR (CDCl3) δ 7.84 (1H, d, J=8.4 Hz), 7.58 (1H, d, J=8.8 Hz), 7.09 (2H, m), 6.98 (1H, d, J=8. Hz), 3.06 (6H, s), 2.66 (3H, s); 13C NMR (CDCl3) δ 159.3, 151.5, 149.9, 135.8, 128.6, 119.2, 118.2, 115.5, 106.8, 40.8, 25.6; FTIR (neat) 2918, 2804, 1620, 1600, 1514, 1379, 1155, 1062, 827 cm−1.

Provenance & Evidence