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tert-Butoxy bis(dimethylamino)methane → 2-[2-(Dimethylamino)ethenyl]-1,6-dihydro-6-oxo-3-pyridinecarbonitrile

HRID 542511
Notes
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Reaction equation

HRID 542511 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methane2×HCID 113785166-Hydroxy-2-methylnicotinonitrile

Product 1

HCID 544759082-[2-(Dimethylamino)ethenyl]-1,6-dihydro-6-oxo-3-pyridinecarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. temperaturethe reaction mixture was heated
  2. temperaturethe reaction mixture was heated
  3. stirringwith stirring
  4. temperatureto reflux for 90 minutes
  5. temperatureto cool to room temperature
  6. waitstand overnight
  7. temperatureThe mixture was chilled
  8. customthe separated product was collected
  9. washwashed with chilled ethanol
  10. customdried in a vacuum oven at 90° C.

Sources & evidence

ORD record
ord-6c5d6854b5854fbe846e2873d1371972
Source dataset
uspto-grants-1987_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04657915

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes