Methanol → 6-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[C:9]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=[CH:10]N(C)C.[C:22]([CH2:24][C:25]([NH2:27])=[O:26])#[N:23].CO.[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:27][C:25](=[O:26])[C:24]([C:22]#[N:23])=[CH:10][C:9]=1[C:14]1[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
To the product of step B was added 2-cyanoacetamide (1.912 g, 22.74 mmol), methanol (1.84 mL, 45.5 mmol) and DMF (50 mL). This solution was cannulated into a slurry of NaH (2.067 g, 51.7 mmol, 60% dispersion in mineral oil, washed with hexane) and DMF (24 mL) and then heated to 95° C. for 2.5 hours. The reaction was cooled and then concentrated in vacuo. The residue was diluted with ethyl acetate and then washed with 10% aq. NaHSO4 and water. The organic portion was dried (Na2SO4) and concentrated before suspending the solid in hot ethanol. After cooling, the solid was filtered and washed with ethanol and then hexane. This afforded product. MS (electrospray) m/e 341.1 MH+ (Rt=3.1 min LC/MS).
Workup
- temperatureThe reaction was cooled
- concentrationconcentrated in vacuo
- additionThe residue was diluted with ethyl acetate
- washwashed with 10% aq. NaHSO4 and water
- dry with materialThe organic portion was dried (Na2SO4)
- concentrationconcentrated
- temperatureAfter cooling
- filtrationthe solid was filtered
- washwashed with ethanol
Sources & evidence
- ORD record
- ord-9a1112992949421cae57ac88c6a9a6d6
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07271266B2
Reaction notes
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