Ethanol → HCID 178502673, compound

Participants

Reaction Conditions

Reaction Steps

Add 6-hydroxy-nicotinoyl chloride (11.2 g, 71 mmol) and N,O-dimethylhydroxylamine hydrochloride (7.76 g, 79.5 mmol) to ethanol-free chloroform (100 mL, wash chloroform with water, dry over MgSO4, then filter through neutral alumina to obtain ethanol-free chloroform). Cool the mixture to 0° C. under a nitrogen atmosphere. Add pyridine (12.6 mL, 155.8 mmol), warm reaction up to room temperature and stir for 16 h under a nitrogen atmosphere. Wash reaction with water (2×75 mL) followed by brine (75 mL). Dry the organic layer over MgSO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with DCM/2M ammonia in methanol (44:1) to obtain the desired intermediate as a yellow solid (8.6 g, 67%). MS (ES+) m/z: 183.2 (M+H)+.

Provenance & Evidence