N,O-Dimethylhydroxylamine → HCID 50994266, compound

Participants

Reaction Conditions

Reaction Steps

To 0.500 g (2.91 mmol) 2-chloro-6-methyl-isonicotinic acid in 5.0 mL of anhydrous methylene chloride and 0.5 mL of anhydrous DMF was added 0.47 g (3.5 mmol) 1-hydroxybenzotriazole hydrate. The reaction mixture was stirred for 20 minutes at 0° C. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.67 g, 3.5 mmol) was added to the reaction mixture. Stirring was continued for 1 hour allowing the reaction mixture to slowly warm up to room temperature. The reaction mixture was re-cooled to 0° C. and 0.750 g (5.8 mmol) of diisopropylethylamine and 0.340 g (3.5 mmol) of O,N-dimethyl-hydroxylamine were added. The reaction mixture was allowed to warm to room temperature and was stirred overnight. The reaction mixture was diluted with water and extracted with 50 mL of methylene chloride. The organic phase was washed with water, and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was chromatographed on silica gel using 5:1 hexane:ethyl acetate to give 360 mg of the 2-chloro-N-methoxy-6,N-dimethyl-isonicotinamide.

Provenance & Evidence