Water → 6-(3-Hydroxypropoxy)nicotinonitrile

HRID 2424971Notes

Reaction equation

HRID 2424971 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[CH2:4][CH2:5][OH:6].Cl[C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][N:10]=1.O>CN(C=O)C>[OH:6][CH2:5][CH2:4][CH2:3][O:7][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 104421,3-PropanediolHCID 24758Sodium hydrideHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 431521396-(3-Hydroxypropoxy)nicotinonitrileYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.42 g, 60% suspension in mineral oil, 10.61 mmol) was added to a solution of 1,3-propanediol (2.30 mL, 31.83 mmol) in DMF (22 mL) at 0° C., and the mixture was stirred at rt for 20 minutes. To the resultant pale yellow slurry was added 6-chloronicotinonitrile (1.50 g, 10.61 mmol) in one portion. The mixture was stirred at rt for 18 h. It was then poured into water. The precipitates were filtered and the filtrate was extracted with ethyl acetate. The organic extract was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the title compound (1.56 g, 83%) as a white solid. 1H NMR (300 MHz, CD2Cl2) δ 8.47 (d, 1H), 7.82-7.79 (m, 1H), 6.84-6.82 (m, 1H), 4.53 (t, 2H), 3.75 (t, 2H), 2.06-1.99 (m, 2H).

Workup

  1. stirringThe mixture was stirred at rt for 18 h
  2. filtrationThe precipitates were filtered
  3. extractionthe filtrate was extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-314f78868fce45e28a6c9f5f27fa2dbd
Source dataset
uspto-grants-2011_06
Patent number
US07964622B2

Reaction notes

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