Nitromethane → HCID 67288650, compound

HRID 1626444Notes

Reaction equation

HRID 1626444 reaction equation
[CH3:1][O:2][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+:15]([CH3:18])([O-:17])=[O:16].Cl.CN.C([O-])(=O)C.[Na+]>>[CH3:1][O:2][C:3]1[C:4]([CH:5]=[CH:18][N+:15]([O-:17])=[O:16])=[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 582594802-Methoxy-6-(trifluoromethyl)-3-pyridinecarboxaldehyde

Product 1

HCID 67288650HCID 67288650, compoundYield 53.3%

Procedure

2-methoxy-6-(trifluoromethyl)nicotinaldehyde (300 mg, 1.46 mmol) (Example 139, Step A) was treated with nitromethane (790 μl, 14.6 mmol) at ambient temperature. Solid methylamine hydrochloride (77.0 mg, 1.14 mmol) and sodium acetate (93.6 mg, 1.14 mmol) were added and the colorless reaction mixture was stirred rapidly at ambient temperature for 14 hours. The reaction mixture was applied directly to silica gel and eluted with 2 to 20% ethyl acetate-hexanes to provide the desired compound (193 mg, 0.778 mmol, 53.2% yield) as a yellow solid.

Workup

  1. washeluted with 2 to 20% ethyl acetate-hexanes

Sources & evidence

ORD record
ord-9df7b7532309447e84c030998055c833
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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