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

HRID 2115641Notes

Reaction equation

HRID 2115641 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-78a48532ed904309b97e9dfdf9bb7656
Source dataset
uspto-grants-2008_10
Patent number
US07435743B2

Reaction notes

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