Phosphorus oxychloride → HCID 117770287, compound
Reaction equation
P(Cl)(Cl)([Cl:3])=O.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[C:18]([CH3:19])=[CH:17][C:16](O)=[C:15]([C:21]#[N:22])[C:14]1=[O:23].C(=O)([O-])O.[Na+]>CN(C)C=O>[Cl:3][C:16]1[CH:17]=[C:18]([CH3:19])[N:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[Cl:6])[C:14](=[O:23])[C:15]=1[C:21]#[N:22]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Phosphorus oxychloride (2.59 mL) was slowly added to N,N-dimethylformamide (17.8 mL) under ice-cooling, and the mixture was stirred for 15 min. To the reaction mixture was added a solution of 1-(2-chlorophenyl)-4-hydroxy-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step D (2.90 g) in N,N-dimethylformamide (4.50 mL) under ice-cooling, and the reaction mixture was heated overnight at 80° C. The reaction mixture was cooled to room temperature, and poured into ice water, and the mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized from ethyl acetate/hexane to give the title compound (2.50 g).
Workup
- temperaturecooling
- temperaturecooling
- temperatureThe reaction mixture was cooled to room temperature
- extractionextracted with ethyl acetate
- washThe extract was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was recrystallized from ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-42c97030dd854a77a824d07df79cde0b
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09085578B2
Reaction notes
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