Methanol → HCID 69482820, compound

HRID 2364217Notes

Reaction equation

HRID 2364217 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]2[CH:11]=[C:12]([N+:19]([O-:21])=[O:20])[C:13]([C:16](N)=[O:17])=[N:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:22][OH:23]>>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]2[CH:11]=[C:12]([N+:19]([O-:21])=[O:20])[C:13]([C:16]([O:23][CH3:22])=[O:17])=[N:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

3

Reactant 2

HCID 887MethanolHCID 69480151HCID 69480151, compound

Product 1

HCID 69482820HCID 69482820, compound

Procedure

To a mixture of 5-[(3,4-difluorophenyl)methyl]-3-nitro-2-pyridinecarboxamide (2.7 g, 9.21 mmol) and MeOH (100 ml), was added dimethylformamidedimethylacetal (3.29 g, 27.62 mmol). After stirring at room temperature overnight, the solvent was evaporated using no heat, EtOAc was added and the organic layer was washed three times with brine, dried and concentrated in vacuo. The product was purified by chromatography on silica gel, eluting with 20-60% EtOAc/hexanes to afford a dark brown oil. 1H NMR (CDCl3) δ 8.71 (1H, s), 8.05 (1H, s), 7.20-7.15 (1H, m), 7.00-6.80 (2H, m), 4.10 (2H, s), 4.01 (3H, s); HRMS calcd for C14H10F2N2O4+H+: 309.0687. Found 309.0681.

Workup

  1. additionwas added dimethylformamidedimethylacetal (3.29 g, 27.62 mmol)
  2. customthe solvent was evaporated
  3. additionwas added
  4. washthe organic layer was washed three times with brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by chromatography on silica gel
  8. washeluting with 20-60% EtOAc/hexanes
  9. customto afford a dark brown oil

Sources & evidence

ORD record
ord-7eb932202fdf489ab7da6d6ae5eec572
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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