N,O-Dimethylhydroxylamine → HCID 50994266, compound

Temperature

0 °C

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.

1. stirringStirring
2. waitwas continued for 1 hour
3. temperatureto slowly warm up to room temperature
4. temperatureThe reaction mixture was re-cooled to 0° C.
5. temperatureto warm to room temperature
6. stirringwas stirred overnight
7. extractionextracted with 50 mL of methylene chloride
8. washThe organic phase was washed with water, and brine
9. dry with materialdried over anhydrous sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated
12. customThe crude product was chromatographed on silica gel using 5:1 hexane

ORD record

ord-a8fc32e507c447a2a572342e7c9afc4b

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07504401B2