Water → 6-(3-Hydroxypropoxy)nicotinonitrile

HRID 603448Notes

Reaction equation

HRID 603448 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, 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 min. To the resultant heterogeneous mixture was added 6-chloronicotinonitrile (1.50 g, 10.6 mmol) in one portion. The mixture was stirred at rt for 18 h, poured into water, and filtered. The filtrate was extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), and concentrated under reduced pressure to give the product (1.56 g, 83%) as a white solid. 1H NMR (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. filtrationfiltered
  3. extractionThe filtrate was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f7633a5486764f33b239a73efeb877a7
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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