Imidazole → 5-(4-Imidazol-1-yl-phenyl)-6-methyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile
Reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:16]#[N:17])[C:11](=[O:15])[NH:12][C:13]=2[CH3:14])=[CH:4][CH:3]=1.[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1.C(=O)([O-])[O-].[K+].[K+]>O.[Cu].[Cu]I>[N:18]1([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:9]=[C:10]([C:16]#[N:17])[C:11](=[O:15])[NH:12][C:13]=3[CH3:14])=[CH:4][CH:3]=2)[CH:22]=[CH:21][N:20]=[CH:19]1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 200 °C
Procedure
A mixture of 1,2-dihydro-5-(4-fluorophenyl)-6-methyl-2-oxo-3-pyridinecarbonitrile (5.0 grams), imidazole (25 grams), potassium carbonate (5 grams), copper (0.5 grams) and copper (I) iodide (0.5 grams) is heated just at 200° C. for 24 hours and then at 260° C. for 8 hours. After cooling, the reaction mixture is diluted with water and filtered. The filtrate is acidified with 6N hydrochloric acid and the precipitate is collected. This solid is boiled in 1 liter of methanol and the hot mixture is filtered. The filtrate is evaporated to a volume of 200 ml and cooled to give 0.7 grams of 1,2-dihydro-5-[4-(1H-imidazol-1-yl)phenyl]-6-methyl-2-oxo-3-pyridinecarbonitrile: mp 300°-301° C.
Workup
- temperatureAfter cooling
- filtrationfiltered
- customthe precipitate is collected
- filtrationthe hot mixture is filtered
- customThe filtrate is evaporated to a volume of 200 ml
- temperaturecooled
Sources & evidence
- ORD record
- ord-08e76e93f88c40a28e52a06f37a6a94d
- Source dataset
- uspto-grants-1985_03
- Patent number
- US04503061
Reaction notes
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