Nitromethane → HCID 67287927, compound

HRID 1626531Notes

Reaction equation

HRID 1626531 reaction equation
[CH:1]1([C:4]2[CH:11]=[CH:10][C:7]([CH:8]=O)=[C:6]([N:12]([CH3:14])[CH3:13])[N:5]=2)[CH2:3][CH2:2]1.[N+:15]([CH3:18])([O-:17])=[O:16].Cl.CN.C([O-])(=O)C.[Na+]>>[CH:1]1([C:4]2[N:5]=[C:6]([N:12]([CH3:14])[CH3:13])[C:7](/[CH:8]=[CH:18]/[N+:15]([O-:17])=[O:16])=[CH:10][CH:11]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 6375NitromethaneHCID 517045Sodium AcetateHCID 6364545Methylamine hydrochlorideHCID 86664401HCID 86664401, compound

Product 1

HCID 67287927HCID 67287927, compoundYield 100.2%

Procedure

6-cyclopropyl-2-(dimethylamino)nicotinaldehyde (100 mg, 0.526 mmol) was diluted with nitromethane (199 μL, 3.68 mmol) followed by the addition of methylamine hydrochloride (21.3 mg, 0.315 mmol) and sodium acetate (25.9 mg, 0.315 mmol). After stirring for 4 hours, the reaction was loaded directly onto a silica gel column and eluted with 5% ethyl acetate/hexanes to 100% ethyl acetate hexanes to yield (E)-6-cyclopropyl-N,N-dimethyl-3-(2-nitrovinyl)pyridin-2-amine (123 mg, 0.527 mmol, 100% yield).

Workup

  1. washeluted with 5% ethyl acetate/hexanes to 100% ethyl acetate hexanes

Sources & evidence

ORD record
ord-fd39e83a9cf84597aa23a080b903bcc9
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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