Methanol → HCID 68671638, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 167 mg of 2-(dimethylamino)-6-(hydroxymethyl)-N,N-dimethylisonicotinamide in 2 mL of H2SO4 and 1.2 mL of H2O was stirred at 135° C. for 12.5 h. The temperature was decreased to 95° C., methanol (5 mL) was added, and the solution was heated for 1 h. The solution was added to ice with H2O and EtOAc, and solid NaHCO3 and sat. NaHCO3 solution were added to pH=8. The aqueous layer was extracted with EtOAc (4×), and the combined extracts were washed with brine (50 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (30% EtOAc/hexanes) provided 102 mg of methyl 2-(dimethylamino)-6-(hydroxymethyl)isonicotinate as a yellow solid in 65% yield.

Provenance & Evidence