Pyridine → 2-(Hydroxymethyl)-6-methylpyridine-4-carbonitrile

Participants

Reaction Steps

To a suspension of 2-hydroxymethyl-6-methyl-isonicotinamide (390 mg, 2.38 mmol) and pyridine (922 mg, 9.50 mmol) in DCM (80 mL), trifluoroacetic anhydride (1.25 g, 5.94 mmol) is added dropwise at 0° C. The mixture is stirred at rt for 1 h and becomes clear before it is carefully diluted with water and DCM. The mixture is washed twice with sat. aq. NaHCO3-solution. The washings are extracted twice with DCM. The combined org. extracts are dried over MgSO4, filtered and concentrated and briefly dried under HV to give crude 2-hydroxymethyl-6-methyl-isonicotinonitrile (544 mg, contains pyridine) as a brownish oil; LC-MS: tR=0.54 min, [M+1]+=148.99; 1H NMR (CDCl3): δ 2.66 (s, 3H), 3.48 (s br, 1H), 5.48 (s, 2H), 7.41 (s, 2H).

Provenance & Evidence