Benzyl Alcohol → 3-(Benzyloxy)pyridine-4-carbonitrile

HRID 884991Notes

Reaction equation

HRID 884991 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:12]1[CH:19]=[N:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15]>CN(C=O)C>[CH2:3]([O:10][C:12]1[CH:19]=[N:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 106783063-Chloropyridine-4-carbonitrile

Product 1

HCID 108223413-(Benzyloxy)pyridine-4-carbonitrileYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.59 g of 60% sodium hydride (in oil) and 5 ml of DMF was stirred while ice-cooling. To the reaction mixture, 1.59 g of benzyl alcohol was added. The reaction mixture was stirred at the same temperature for 10 minutes. To the reaction mixture, 2.0 g of 3-chloroisonicotinonitrile was added, and the reaction mixture was stirred at the same temperature for 30 minutes and at room temperature for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and then to ethyl acetate was added to the reaction mixture, followed by filtration of insoluble matters. The filtrate was concentrated under reduced pressure and the resultant residue was subjected to silica gel column chromatography to give 2.64 g of 3-benzyloxy isonicotinonitrile.

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at the same temperature for 10 minutes
  3. stirringthe reaction mixture was stirred at the same temperature for 30 minutes and at room temperature for 1.5 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. additionto ethyl acetate was added to the reaction mixture
  6. filtrationfollowed by filtration of insoluble matters
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4f97808bfcd3483f8bb485039cabb971
Source dataset
uspto-grants-2012_08
Patent number
US08242133B2

Reaction notes

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