Reaction equation
Cl.[NH2:2][OH:3].C(=O)([O-])[O-].[Na+].[Na+].[CH3:10][N:11]1[C:15]([C:16](=O)[C:17]#[C:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)=[CH:14][CH:13]=[N:12]1>CO>[OH:3][N:2]=[C:16]([C:15]1[N:11]([CH3:10])[N:12]=[CH:13][CH:14]=1)[C:17]#[C:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
An aqueous solution (3.0 mL) of hydroxylamine hydrochloride (338 mg) and an aqueous solution (4.0 mL) of sodium carbonate (515 mg) were added to a methanol (40 mL) solution of 1-(1-methyl-1H-pyrazol-5-yl)-3-[4-(trifluoromethyl)phenyl]prop-2-yn-1-one (338 mg) at a room temperature, and the obtained solution was then stirred overnight. Thereafter, the reaction solution was concentrated under a reduced pressure, and water was then added to the residue, followed by extraction with chloroform. The organic layer was washed with a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=10:0 to 5:5), so as to obtain the title compound (312 mg) in the form of a yellow oily substance.
Workup
- concentrationThereafter, the reaction solution was concentrated under a reduced pressure, and water
- additionwas then added to the residue
- extractionfollowed by extraction with chloroform
- washThe organic layer was washed with a saturated saline
- dry with materialwas then dried over anhydrous magnesium sulfate
- concentrationfollowed by vacuum concentration
- customThe residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=10:0 to 5:5)
Sources & evidence
- ORD record
- ord-e9281dc8cfb3492db2aff26406bcd576
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642626B2
Linked notes
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