Dimethylformamide → HCID 22241493, compound

Participants

Reaction Steps

2-Chloromethyl-quinoline hydrochloride (2.24 g, 10.5 mmol), 4-(hydroxymethyl)-imidazole hydrochloride (1.35 g, 10 mmol) and K2CO3 (4.2 g, 30 mmol) are dissolved/suspended in anhyd. DMF (20 mL) and heated to 100° C. with rapid stirring overnight. The reaction is cooled to r.t. and poured into water (400 mL) and extracted with chloroform (3×150 mL). The organic fractions are pooled and washed with brine (2×200 mL), dried over MgSO4, filtered and reduced under vacuum to an oil. The crude material is purified by flash chromatography (silica, 5% methanol in dichloromethane) to give (3-quinolin-2-ylmethyl-3H-imidazol-4-yl)-methanol and (1-quinolin-2-ylmethyl-1H-imidazol-4-yl)-methanol in a 2:3 ratio. The identity of each regioisomer was determined by NMR NOE experiments. MS (ESI) 240 (M+H)+ found for both regioisomers.

Provenance & Evidence