Ammonia → HCID 55281675, compound

Participants

Reaction Conditions

Reaction Steps

A bomb was charged with 2 (30.0 g, 0.190 mol) and aqueous conc NH3 (225 mL) and the resulting mixture was heated at 210° C. for 20 h. The system was cooled to room temperature, the volatiles removed in vacuo and the residue purified by column chromatography (dichloromethane: 0.4N NH3 in MeOH 9:1) to give (2-amino-6-methyl pyridine-4-yl)-methanol as a mixture of free base and hydrochloride salt. The mixture was redissolved in dichloromethane:i-PrOH 1:1 (1 L) and treated with 20% aqueous NaOH (500 mL). The layers were separated and the organic phase extracted with dichloromethane:i-PrOH 1:1 (1×1 L). The combined organic phase was dried and the solvent evaporated to give (2-amino-6-methyl pyridine-4-yl)-methanol 3 (15.51 g, 59%) as pale orange crystals.

Provenance & Evidence