Nitromethane → (E)-N,N-dimethyl-3-(2-nitrovinyl)-6-(trifluoromethyl)pyridin-2-amine

Reaction equation

[CH3:1][N:2]([CH3:15])[C:3]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[N+:16]([CH3:19])([O-:18])=[O:17].Cl.CN.C([O-])(=O)C.[Na+]>>[CH3:1][N:2]([CH3:15])[C:3]1[C:4](/[CH:5]=[CH:19]/[N+:16]([O-:18])=[O:17])=[CH:7][CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=1

Participants

Reactant 4

HCID 6375Nitromethane

HCID 517045Sodium Acetate

HCID 6364545Methylamine hydrochloride

HCID 582590702-(Dimethylamino)-6-(trifluoromethyl)pyridine-3-carbaldehyde

Product 1

HCID 67287008(E)-N,N-dimethyl-3-(2-nitrovinyl)-6-(trifluoromethyl)pyridin-2-amineYield 66.8%

Procedure

2-(dimethylamino)-6-(trifluoromethyl)nicotinaldehyde (50 mg, 0.229 mmol) was diluted with nitromethane (86.9 μl, 1.60 mmol) followed by the addition of methylamine hydrochloride (9.28 mg, 0.138 mmol) and sodium acetate (11.3 mg, 0.138 mmol). After stirring for 5 hours, the reaction was loaded directly onto silica gel and eluted with 5% ethyl acetate/hexanes to 50% ethyl acetate hexanes to yield the desired compound (40 mg, 0.153 mmol, 66.8% yield).