Dimethylformamide → 5-Methoxypyridine-2-carbonitrile

HRID 418849Notes

Reaction equation

HRID 418849 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+]>O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][N:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 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 Mel (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 (175mg, 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-4cd93c5962ad47c697b199866145b982
Source dataset
uspto-grants-2012_01
Patent number
US08093273B2

Reaction notes

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