2,6-Diaminopyridine → 1,8-Naphthyridin-2-amine, 5-methyl-7-(trifluoromethyl)-

HRID 437391Notes

Reaction equation

HRID 437391 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[N:3]=1.[CH3:9][C:10]([CH2:12][C:13]([C:15]([F:18])([F:17])[F:16])=O)=O>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]2[C:4](=[N:8][C:13]([C:15]([F:18])([F:17])[F:16])=[CH:12][C:10]=2[CH3:9])[N:3]=1.[NH2:1][C:2]1[CH:7]=[CH:6][C:5]2[C:4](=[N:8][C:10]([CH3:9])=[CH:12][C:13]=2[C:15]([F:18])([F:17])[F:16])[N:3]=1

Participants

4

Reactant 2

HCID 88612,6-DiaminopyridineHCID 739431,1,1-Trifluoro-2,4-pentanedione

Product 2

HCID 122730761,8-Naphthyridin-2-amine, 5-methyl-7-(trifluoromethyl)-HCID 122730771,8-Naphthyridin-2-amine, 7-methyl-5-(trifluoromethyl)-

Procedure

A process as claimed in claim 1 wherein 2,6-diaminopyridine is reacted with 1,1,1-trifluoroacetylacetone and the 2-amino-5-methyl-7-trifluoromethyl-1,8-naphthyridine and 2-amino-5-trifluoromethyl-7-methyl-1,8-naphthyridine thus obtained converted to the 2-oxo analogs by reaction with an alkali metal nitrite in the presence of trifluoroacetic acid or pentafluoropropionic acid to provide 5-methyl-7-trifluoromethyl-1,8-naphthyridin-2(1H)-one and 5-trifluoromethyl-7-methyl-1,8-naphthyridin-2(1H)-one.

Sources & evidence

ORD record
ord-096c7e4f1a8645519da44af21ed3ca6a
Source dataset
uspto-grants-1977_06
Patent number
US04031103

Reaction notes

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