Dimethylformamide → HCID 59712225, compound

HRID 1874335Notes

Reaction equation

HRID 1874335 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.F[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 98231-Fluoro-3-nitrobenzeneHCID 11430Potassium CarbonateHCID 142752-Methyl-5-hydroxypyridine

Product 1

HCID 59712225HCID 59712225, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 6-methylpyridin-3-ol (17.6 g, 161 mmol), 1-fluoro-3-nitrobenzene (25.0 g, 177 mmol), potassium carbonate (66.8 g, 483 mmol) and N,N-dimethylformamide (200 mL) was stirred at 90° C. for 13 hr, 120° C. for 5 hr and 140° C. for 4 hr. The reaction mixture was diluted with water and extracted with ethyl acetate (×3). The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was dried to give the title compound (28.6 g, 77%) as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate (×3)
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was dried

Sources & evidence

ORD record
ord-e3958d21dbd14cbc916621fe3ea302fa
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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