Hydroxyamine hydrochloride → 4-(2,2,2-Trifluoro-1-methoxyethyl)pyridine-2-carboxamide
Reaction equation
C(=O)(O)[O-:2].[Na+].Cl.NO.[F:9][C:10]([F:23])([F:22])[CH:11]([C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20]#[N:21])[CH:15]=1)[O:12][CH3:13]>C(O)C>[F:23][C:10]([F:9])([F:22])[CH:11]([C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20]([NH2:21])=[O:2])[CH:15]=1)[O:12][CH3:13]Participants
5
Procedure
To 2 ml of ethanol were added 0.12 g of sodium bicarbonate and 0.1 g of hydroxylamine hydrochloride, and the mixture was heated to reflux for 1 hour. After allowing to cool, 0.2 g of 4-(2,2,2-thfluoro-1-methoxyethyl)pyridine-2-carbonitrile was added at 0° C., and the mixture was stirred for 3 hours, and concentrated. To the residue was added water, the resultant solution was extracted with ethyl acetate three times, and the organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.15 g of 4-(2,2,2-trifluoro-1-methoxyethyl)pyridine-2-carboxamide=oxime.
Workup
- temperaturethe mixture was heated
- temperatureto reflux for 1 hour
- temperatureto cool
- concentrationconcentrated
- additionTo the residue was added water
- extractionthe resultant solution was extracted with ethyl acetate three times
- washwashed with an aqueous saturated sodium chloride solution
- dry with materialdried with anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-07a4137ff4f3490bb328c7a1ec6f5d24
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318776B2
Reaction notes
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