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

HRID 1626481Notes

Reaction equation

HRID 1626481 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

5

Reactant 4

HCID 6375NitromethaneHCID 517045Sodium AcetateHCID 6364545Methylamine hydrochlorideHCID 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).

Workup

  1. washeluted with 5% ethyl acetate/hexanes to 50% ethyl acetate hexanes

Sources & evidence

ORD record
ord-f1b0f7680e5f4ff59db6738c2e1cb1d7
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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