3-Hydroxypyridine → HCID 43087651, compound

HRID 2232980Notes

Reaction equation

HRID 2232980 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([OH:7])[CH:2]=1.[H-].[Na+].Cl[C:11]1[N:18]=[CH:17][CH:16]=[CH:15][C:12]=1[C:13]#[N:14]>CN(C)C=O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:11]2[N:18]=[CH:17][CH:16]=[CH:15][C:12]=2[C:13]#[N:14])[CH:2]=1

Participants

5

Reactant 3

HCID 79713-HydroxypyridineHCID 24758Sodium hydrideHCID 810792-Chloronicotinonitrile

Product 1

HCID 43087651HCID 43087651, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of pyridin-3-ol (1.3 g, 10 mmol) in N,N-dimethyl formamide (25 ml) was added 60 % NaH in mineral oil (0.3 g, 15 mmol) and 2-chloronicotinonitrile (1.38 g, 10 mmol) and heated at 120° C. for overnight. The reaction mixture was quenched with 1M NaHCO3 and extracted with ethyl acetate (3×30 ml). The combined organic extracts were washed with saturated NaCl (50 ml), dried (Na2SO4), filtered and concentrated. The crude product was purified by flash column chromatography using dichloromethane to yield 1.1 g (50%) of product. MS (ESI+) m/z 198 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with 1M NaHCO3
  2. extractionextracted with ethyl acetate (3×30 ml)
  3. washThe combined organic extracts were washed with saturated NaCl (50 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-9d64255db3124a92ae5e7fb7f88a28ce
Source dataset
uspto-grants-2010_05
Patent number
US07709469B2

Reaction notes

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