Dimethylformamide → 5-Methoxypyridine-2-carbonitrile

HRID 884703Notes

Reaction equation

HRID 884703 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][N:4]=1)#[N:2].[CH3:10]N(C=O)C.C([O-])([O-])=O.[K+].[K+].CI>O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][N:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 214137735-Hydroxypyridine-2-carbonitrile

Product 1

HCID 131442795-Methoxypyridine-2-carbonitrileYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Cyano-5-hydroxy pyridine (200 mg, 1.66 mmol), DMF (10 mL) and K2CO3 (253 mg, 1.83 mmol), and MeI (354 mg, 2.49 mmol) were combined at rt and the reaction mixture was stirred for 24 h at rt. The reaction mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed with water, dried and concentrated to give 2-cyano-5-methoxy pyridine (175 mg, 78%).

Workup

  1. customwere combined at rt
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ec94e077f7d5473e8837e20a118c1ece
Source dataset
uspto-grants-2012_08
Patent number
US08242130B2

Reaction notes

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