Cyanoacetamide → 5-(2-Chlorophenyl)-1,2-dihydro-2-oxo-3-pyridinecarbonitrile

HRID 1733566Notes

Reaction equation

HRID 1733566 reaction equation
C[O-].[Na+].[C:4]([CH2:6][C:7]([NH2:9])=[O:8])#[N:5].[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17](=[CH:20]N(C)C)[CH:18]=O>CO>[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:20]=[C:6]([C:4]#[N:5])[C:7](=[O:8])[NH:9][CH:18]=1

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 10942334Sodium MethoxideHCID 542093582-(2-Chlorophenyl)-3-dimethylaminoprop-2-enal

Product 1

HCID 136055345-(2-Chlorophenyl)-1,2-dihydro-2-oxo-3-pyridinecarbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In the manner described in Example 6, a solution of 48.6 g. of sodium methoxide and 42.0 g. of cyanoacetamide in 1000 ml. of methanol and 93.6 g. of 2-(2-chlorophenyl)-3-(dimethylamino)-2-propenal is refluxed for 16 hours to yield 30.0 g. of a tan solid. The solid is recrystallized from ethanol to yield the product of the Example as white needles, m.p. 252°-254° C.

Workup

  1. customto yield 30.0 g
  2. customThe solid is recrystallized from ethanol
  3. customto yield the product of the Example as white needles, m.p. 252°-254° C.

Sources & evidence

ORD record
ord-dc5235097d1e4403a335e5ef446edf9b
Source dataset
uspto-grants-1980_12
Patent number
US04242515

Reaction notes

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