Phosphorus oxychloride → 4-Chloro-1-(2-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[C:4](=[O:15])[C:3]=1[CH:16]=[N:17]O.P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[C:4](=[O:15])[C:3]=1[C:16]#[N:17]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 4-chloro-1-(2-chlorophenyl)-3-((hydroxyimino)methyl)pyridin-2(1H)-one obtained in Step C (968 mg) in acetonitrile (6.80 mL) was added phosphorus oxychloride (0.319 mL) at room temperature. The reaction mixture was heated at 90° C. for 1 hr, cooled to room temperature, and poured into ice water, and the mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution under ice-cooling. The aqueous layer was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (891 mg). 1H NMR (400 MHz, CDCl3) δ 6.47 (1H, d, J=7.6 Hz), 7.35 (1H, dd, J=7.6, 1.6 Hz), 7.39 (1H, d, J=7.6 Hz), 7.42-7.50 (2H, m), 7.60 (1H, dd, J=7.6, 1.6 Hz).
Workup
- temperaturecooled to room temperature
- temperaturecooling
- extractionThe aqueous layer was extracted with ethyl acetate
- washThe extract was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-70dc3c0cefee448fbebfca75fcc2c4cc
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09085578B2
Reaction notes
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