Dimethylformamide → 2-[2-(Dimethylamino)-1-propenyl]-6-methoxy-3-pyridinecarbonitrile

HRID 979999Notes

Reaction equation

HRID 979999 reaction equation
COC1N=CC(C#N)=CC=1.[CH3:11][O:12][C:13]1[N:18]=[C:17]([CH3:19])[C:16]([C:20]#[N:21])=[CH:15][CH:14]=1.CO[C:24](OC)([N:26]([CH3:28])[CH3:27])[CH3:25].CN(C)C=O>CO>[CH3:27][N:26]([CH3:28])[C:24]([CH3:25])=[CH:19][C:17]1[C:16]([C:20]#[N:21])=[CH:15][CH:14]=[C:13]([O:12][CH3:11])[N:18]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 27367762-Methoxy-5-pyridinecarbonitrileHCID 137499186-Methoxy-2-methylpyridine-3-carbonitrile

Product 1

HCID 543079292-[2-(Dimethylamino)-1-propenyl]-6-methoxy-3-pyridinecarbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

2-2-(Dimethylamino)-1-propenyl]-6-methoxy-3-pyridinecarbonitrile--A mixture containing 47.2 g of 6-methoxy-2-methyl-3-pyridinecarbonitrile, 100 ml of dimethylacetamide dimethyl acetal and 100 ml of dimethylformamide was heated with stirring in an oil bath at 130° C. for 1 hour and 45 minutes. The temperature of the oil bath was raised to 150° C. and the methanol formed by the reaction was distilled off using a 12" distillation column (Vigreux) while continuing the heating at 150° C. for 14 hours. The reaction mixture was concentrated, 50 ml of ether was added to the concentrated solution whereupon the product crystallized out. The mixture was chilled and the crystalline solid collected. The solid was washed with cold ether, dried and recrystallized from ethyl acetate using decolorizing charcoal to yield 33.5 g of 2-[2-(dimethylamino)-1-propenyl]-6-methoxy-3-pyridinecarbonitrile, m.p. 103°-104° C.

Workup

  1. temperaturewas heated
  2. temperatureThe temperature of the oil bath was raised to 150° C.
  3. distillationwas distilled off
  4. distillationa 12" distillation column (Vigreux)
  5. customheating at 150° C.
  6. customfor 14 hours
  7. concentrationThe reaction mixture was concentrated
  8. addition50 ml of ether was added to the concentrated solution whereupon the product
  9. customcrystallized out
  10. temperatureThe mixture was chilled
  11. customthe crystalline solid collected
  12. washThe solid was washed with cold ether
  13. customdried
  14. customrecrystallized from ethyl acetate using

Sources & evidence

ORD record
ord-e6816dcca2d94615bd188fd180027040
Source dataset
uspto-grants-1987_01
Patent number
US04634772

Reaction notes

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