Benzyl Bromide → 3-(Benzyloxy)pyridine-2-carbonitrile

HRID 1611117Notes

Reaction equation

HRID 1611117 reaction equation
[OH:1][C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O>[CH2:16]([O:1][C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1019203-Hydroxypyridine-2-carbonitrile

Product 1

HCID 222589533-(Benzyloxy)pyridine-2-carbonitrileYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 3-hydroxypicolinonitrile (3.00 g, 25.0 mmol), which was prepared according to “Synthesis” 316 (1983) and “J. Org. Chem.” 48 1375 (1983), potassium carbonate (5.40 g, 39.1 mmol) and benzyl bromide (5.10 g, 29.8 mmol) in acetone (150 mL) was stirred at room temperature for 20 hrs. The reaction mixture was filtrated and the filtrate was evaporated. The residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane=1/3 to 1/2) followed by recrystallization from ethyl acetate/n-hexane=1/4 to give 3-benzyloxypicolinonitrile as a colorless solid (4.354 g, yield; 83%).

Workup

  1. customwas prepared
  2. customaccording to “Synthesis” 316 (1983) and “J
  3. filtrationThe reaction mixture was filtrated
  4. customthe filtrate was evaporated
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane=1/3 to 1/2)
  6. customfollowed by recrystallization from ethyl acetate/n-hexane=1/4

Sources & evidence

ORD record
ord-70ca3c0f5927462e9f4ae5fb8ab9d585
Source dataset
uspto-grants-2006_01
Patent number
US06984649B1

Reaction notes

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