tert-Butoxy bis(dimethylamino)methane → 2-[2-(Dimethylamino)ethenyl]-1,6-dihydro-6-oxo-3-pyridinecarbonitrile
Reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:10])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[CH3:11][N:12]([CH:14](N(C)C)OC(C)(C)C)[CH3:13]>CN(C)C=O>[CH3:11][N:12]([CH3:14])[CH:13]=[CH:1][C:2]1[NH:3][C:4](=[O:10])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]Participants
Conditions
- Temperature
- 110 °C
Procedure
To a stirred mixture containing 6.7 g of 1,6-dihydro-2-methyl-6-oxo-3-pyridinecarbonitrile in 100 ml of dimethylformamide was quickly added 11.5 ml of bis(dimethylamino)-t-butoxymethane and the reaction mixture was heated with stirring for 3 hours at 110° C. After a tlc analysis had shown some of the starting material still present, another 2.3 ml of bis(dimethylamino)-t-butoxymethane was added, the reaction mixture was heated with stirring to reflux for 90 minutes, and then allowed to cool to room temperature and stand overnight. The mixture was chilled and the separated product was collected, washed with chilled ethanol and dried in a vacuum oven at 90° C. to yield 8.2 g of 2-[2-(dimethylamino)ethenyl]-1,6-dihydro-6-oxo-3-pyridinecarbonitrile, m.p. 298°-300° C.
Workup
- temperaturethe reaction mixture was heated
- temperaturethe reaction mixture was heated
- stirringwith stirring
- temperatureto reflux for 90 minutes
- temperatureto cool to room temperature
- waitstand overnight
- temperatureThe mixture was chilled
- customthe separated product was collected
- washwashed with chilled ethanol
- customdried in a vacuum oven at 90° C.
Sources & evidence
- ORD record
- ord-6c5d6854b5854fbe846e2873d1371972
- Source dataset
- uspto-grants-1987_04
- Patent number
- US04657915
Reaction notes
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