Acetic Anhydride → 6-[(2-Oxopropyl)amino]pyridine-3-carboxylic acid
Reaction equation
[CH3:1][NH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][N:4]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>>[C:12]([CH2:1][NH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][N:4]=1)(=[O:14])[CH3:13]Participants
3
Procedure
A 1.5 g portion of 6-methylaminonicotinic acid in 20 ml of acetic anhydride was heated under reflux for 1.5 hours. After evaporation of the solvent under reduced pressure, the residue was dissolved with saturated aqueous sodium bicarbonate, and the aqueous layer was washed with ethyl acetate and then adjusted to pH 3 using concentrated hydrochloric acid. Then the aqueous layer was extracted with chloroform, the organic layer was washed and dried, and then the solvent was evaporated under reduced pressure to obtain 280 mg of the title compound as white crystals.
Workup
- temperatureunder reflux for 1.5 hours
- customAfter evaporation of the solvent under reduced pressure
- dissolutionthe residue was dissolved with saturated aqueous sodium bicarbonate
- washthe aqueous layer was washed with ethyl acetate
- extractionThen the aqueous layer was extracted with chloroform
- washthe organic layer was washed
- customdried
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-959d8bb651d44dfabb5de79cbff7b980
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06673799B1
Reaction notes
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