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 eight 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 one 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-5958e949acbc4815b949c4ef0ac9d61c
- Source dataset
- uspto-grants-1986_04
- Patent number
- US04584299
Reaction notes
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