Water → HCID 67328647, compound

Participants

Reaction Steps

A solution containing 340 mg (1.52 mmol) of methyl 6-(Dimethylamino)-4-methoxy-2-methylnicotinate in 5 mL of 6N aq. HCl was stirred at reflux for 16 h. The reaction mixture was poured into 50 mL of water and the pH was set up to 12. The mixture was extracted with two 40-mL portions of ethyl acetate. The combined organic solution was washed with a 40-mL portion of brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (2×6 cm). Elution with 9:1 dichloromethane-methanol afforded the expected product as a colorless oil: yield 87 mg (34%); silica gel TLC Rf 0.25 (9:1 dichloromethane-methanol); 1H NMR (CDCl3) δ 2.33 (s, 3H), 3.02 (s, 6H), 3.75 (s, 3H), 5.77 (s, 1H) and 6.03 (s, 1H); 13C NMR (CDCl3) δ 24.8, 38.0, 38.0, 54.7, 87.4, 98.5, 157.9, 160.8, 167.5; mass spectrum (APCI), m/z 167.1183 (M+H)+ (C9H15N2O requires 167.1184).

Provenance & Evidence