Cyanoacetamide → 1,2-Dihydro-5-(4-fluorophenyl)-6-methyl-2-oxo-3-pyridinecarbonitrile

HRID 364936Notes

Reaction equation

HRID 364936 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]=CN(C)C)[C:9](=O)[CH3:10])=[CH:4][CH:3]=1.[C:17]([CH2:19][C:20]([NH2:22])=[O:21])#[N:18].C[O-].[Na+]>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:19]([C:17]#[N:18])[C:20](=[O:21])[NH:22][C:9]=2[CH3:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 10942334Sodium MethoxideHCID 867399571-(4-Fluorophenyl)-2-(dimethylamino)ethenyl-2-propanone

Product 1

HCID 202385991,2-Dihydro-5-(4-fluorophenyl)-6-methyl-2-oxo-3-pyridinecarbonitrileYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(4-fluorophenyl)-2-(dimethylamino)ethenyl-2-propanone (59.6 grams), cyanoacetamide (26.7 grams) and sodium methoxide (34.3 grams) in 830 ml of dimethylformamide is heated under reflux for two hours and then the reaction mixture is concentrated on a rotary evaporator. The residual solid is suspended in water (2 liters) and is stirred overnight. The aqueous mixture is acidified with 12 N HCl, diluted with water to a volume of 4 liters, and stirred for two hours. The solid product is collected, washed with water (500 ml) and then with ethanol to give 55.4 grams of 1,2-dihydro-5-(4-fluorophenyl)-6-methyl-2-oxo-3-pyridinecarbonitrile.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for two hours
  3. concentrationthe reaction mixture is concentrated on a rotary evaporator
  4. additiondiluted with water to a volume of 4 liters
  5. stirringstirred for two hours
  6. customThe solid product is collected
  7. washwashed with water (500 ml)

Sources & evidence

ORD record
ord-4e9a025afcf04fd4b0fae9a40b8a6052
Source dataset
uspto-grants-1986_08
Patent number
US04607037

Reaction notes

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