Cyanoacetamide → 6-Methyl-2-oxo-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile

HRID 1249315Notes

Reaction equation

HRID 1249315 reaction equation
[CH3:1][C:2]([CH2:4][C:5]([C:7]([F:10])([F:9])[F:8])=O)=O.[C:11]([CH2:13][C:14]([NH2:16])=[O:15])#[N:12].C(C1C(=O)NC(C)=CC=1C)#N.C(C1C(=O)NC(C)=C(C)C=1C)#N.C(CC(=O)C)(=O)C.CC(C(=O)C)C(=O)C>>[C:11]([C:13]1[C:14](=[O:15])[NH:16][C:2]([CH3:1])=[CH:4][C:5]=1[C:7]([F:10])([F:9])[F:8])#[N:12]

Participants

7

Reactant 6

HCID 7898Cyanoacetamide3×HCID 31261AcetylacetoneHCID 698563-Cyano-4,6-dimethyl-2-hydroxypyridineHCID 699493-Methyl-2,4-pentanedioneHCID 739431,1,1-Trifluoro-2,4-pentanedioneHCID 6425082-Hydroxy-4,5,6-trimethylnicotinonitrile

Product 1

HCID 2474406-Methyl-2-oxo-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile

Procedure

3-Cyano-6-methyl-4-trifluoromethylpyrid-2-one was prepared from 1,1,1-trifluoroacetylacetone and cyanoacetamide following the procedure of Kametani and Sato (Yakugaku Kenkyu 34, 117, 1962). 3-Cyano-4,6-dimethylpyrid-2-one and 3-cyano-4,5,6-trimethylpyrid-2-one were similarly prepared from acetylacetone and cyanoacetamide, and 3-methylpentan-2,4-dione and cyanoacetamide respectively.

Sources & evidence

ORD record
ord-f7c615b5ef9c45f6a4010aeb496892f8
Source dataset
uspto-grants-1986_12
Patent number
US04631081

Reaction notes

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