Nitromethane → HCID 67288800, compound

HRID 1626514Notes

Reaction equation

HRID 1626514 reaction equation
[CH:1]1([C:4]2[CH:11]=[CH:10][C:7]([CH:8]=O)=[C:6]([O:12][CH3:13])[N:5]=2)[CH2:3][CH2:2]1.[N+:14]([CH3:17])([O-:16])=[O:15].Cl.CN.C([O-])(=O)C.[Na+]>>[CH:1]1([C:4]2[N:5]=[C:6]([O:12][CH3:13])[C:7](/[CH:8]=[CH:17]/[N+:14]([O-:16])=[O:15])=[CH:10][CH:11]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 6375NitromethaneHCID 517045Sodium AcetateHCID 6364545Methylamine hydrochlorideHCID 83816695HCID 83816695, compound

Product 1

HCID 67288800HCID 67288800, compoundYield 89.8%

Procedure

6-Cyclopropyl-2-methoxynicotinaldehyde (121 mg, 0.683 mmol) was diluted with nitromethane (259 μL, 4.78 mmol) followed by the addition of methylamine hydrochloride (27.7 mg, 0.410 mmol) and sodium acetate (33.6 mg, 0.410 mmol). After stirring for 4 hours, the reaction was loaded directly onto a silica gel column and eluted with 5% ethyl acetate/hexanes to 50% ethyl acetate hexanes to yield (E)-6-cyclopropyl-2-methoxy-3-(2-nitrovinyl)pyridine (135 mg, 0.613 mmol, 89.8% yield).

Workup

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

Sources & evidence

ORD record
ord-88f10ca2f2fc4fc6baf0ad0f38a128d7
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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