Water → HCID 22989699, compound

HRID 1168967Notes

Reaction equation

HRID 1168967 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:11][CH2:12][CH:13]([Br:15])[CH3:14].O>CN(C)C=O>[Br:15][CH:13]([CH3:14])[CH2:12][CH2:11][O:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78891,3-DibromobutaneHCID 79713-HydroxypyridineHCID 24758Sodium hydride

Product 1

HCID 22989699HCID 22989699, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere, a solution of 3-hydroxypyridine (1.00 g, 10.52 mmol) in N,N-dimethylformamide (DMF) (10 mL) was slowly added to a cold (0° C.), stirring slurry of sodium hydride (0.50 g of an 60% dispersion in mineral oil, 12.63 mmol) in DMF (5 mL). After stirring 30 min, 1,3-dibromobutane (2.50 g, 11.57 mmol) was slowly added drop-wise. The resulting mixture was stirred at 0-4° C. for 16 h. Cold water (10 mL) was added, and the mixture was extracted with ether (3×100 mL). The combined ether extracts were dried (Na2SO4), filtered and concentrated by rotary evaporation to give 2.23 g (92.5%) of an oil.

Workup

  1. stirringThe resulting mixture was stirred at 0-4° C. for 16 h
  2. extractionthe mixture was extracted with ether (3×100 mL)
  3. dry with materialThe combined ether extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-251fd9af4229491ea87495226e13d6b9
Source dataset
uspto-grants-2003_09
Patent number
US06627648B1

Reaction notes

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