Nitromethane → (E)-2-cyclopropyl-3-(2-nitrovinyl)-6-(trifluoromethyl)pyridine

HRID 1626524Notes

Reaction equation

[CH:1]1([C:4]2[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:5]=2[CH:6]=O)[CH2:3][CH2:2]1.[N+:16]([CH3:19])([O-:18])=[O:17].Cl.CN.C([O-])(=O)C.[Na+]>>[CH:1]1([C:4]2[C:5](/[CH:6]=[CH:19]/[N+:16]([O-:18])=[O:17])=[CH:8][CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:11]=2)[CH2:3][CH2:2]1

Participants

Reactant 4

HCID 6375Nitromethane

HCID 517045Sodium Acetate

HCID 6364545Methylamine hydrochloride

HCID 866644002-Cyclopropyl-6-(trifluoromethyl)nicotinaldehyde

Product 1

HCID 67287702(E)-2-cyclopropyl-3-(2-nitrovinyl)-6-(trifluoromethyl)pyridineYield 16.7%

Procedure

2-Cyclopropyl-6-(trifluoromethyl)nicotinaldehyde (130 mg, 0.604 mmol) was diluted with nitromethane (229 μL, 4.23 mmol) followed by the addition of methylamine hydrochloride (24.5 mg, 0.363 mmol) and sodium acetate (29.7 mg, 0.363 mmol). After stirring for 4 hours, the reaction was loaded onto silica gel and eluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes to yield (E)-2-cyclopropyl-3-(2-nitrovinyl)-6-(trifluoromethyl)pyridine (26 mg, 0.101 mmol, 16.7% yield).

Workup

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

Sources & evidence

ORD record: ord-ea5c0ceb205f4efeacc5e383cd75a10e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785445B2

Reaction notes

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