Dimethylformamide → HCID 58532486, compound

HRID 1404573Notes

Reaction equation

HRID 1404573 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([CH3:8])=[N:6][CH:7]=1.[CH3:12][N:13]([CH:15]=O)[CH3:14]>>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](/[CH:8]=[CH:12]/[N:13]([CH3:15])[CH3:14])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 250672665-Bromo-2-methyl-3-nitropyridine

Product 1

HCID 58532486HCID 58532486, compoundYield 76%

Procedure

A solution of 5-bromo-2-methyl-3-nitropyridine (3.0 g, 13.8 mmol) and N—N-dimethylformamide-dimethylacetal (DMF-DMA) in 45 ml of DMF was heated at 90° C. for 4 hours, and cooled to room temperature. The solvent was evaporated and the residue dissolved in dichloromethane (DCM), which was washed with saturated NaHCO3 and brine, and chromatographed (EtOAc/Hexanes 1:10) to give a red solid, 2.86 g, in 76% yield.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in dichloromethane (DCM)
  3. washwhich was washed with saturated NaHCO3 and brine
  4. customchromatographed (EtOAc/Hexanes 1:10)
  5. customto give a red solid, 2.86 g

Sources & evidence

ORD record
ord-1b465c6ae878495eb4fad467e87c9f7f
Source dataset
uspto-grants-2014_12
Patent number
US08912330B2

Reaction notes

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