3-(Bromomethyl)pyridine-2-carbonitrile → 3-(Methoxymethyl)picolinonitrile

HRID 254155Notes

Reaction equation

HRID 254155 reaction equation
Br[CH2:2][C:3]1[C:4]([C:9]#[N:10])=[N:5][CH:6]=[CH:7][CH:8]=1.[CH3:11][O-:12].[Na+]>CO>[CH3:11][O:12][CH2:2][C:3]1[C:4]([C:9]#[N:10])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 103754503-(Bromomethyl)pyridine-2-carbonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 629195843-(Methoxymethyl)picolinonitrileYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 3-bromomethylpyridine-2-carbonitrile (591 mg, 3.0 mmol) in MeOH (10 mL) at 0° C. was treated with NaOMe (324 mg, 6.0 mmol), warmed to room temperature, stirred for 2 h, concentrated in vacuo and partitioned between EtOAc (50 mL) and water (30 mL). The organic phase was dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; hexane:EtOAc (9:1-4:1)] to give the title compound (297 mg, 67%) as a clear oil; NMR δH (400 MHz, CDCl3) 3.51 (3H, s), 4.68 (2H, s), 7.50-7.55 (1H, m), 7.92-7.96 (1H, m) and 8.63 (1H, dd, J 5.0, 1.5 Hz); Rf [isohexane:EtOAc (4:1)]=0.65.

Workup

  1. concentrationconcentrated in vacuo
  2. custompartitioned between EtOAc (50 mL) and water (30 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography [SiO2; hexane:EtOAc (9:1-4:1)]

Sources & evidence

ORD record
ord-4cd9a9d045e14d25b26a8eed92f48920
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

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