Dimethylformamide → 5-Methoxypyridine-2-carbonitrile

HRID 1958214Notes

Reaction equation

HRID 1958214 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

To a mixture of 2-cyano-5-hydroxy pyridine (200 mg, 1.66 mmol), DMF (10 mL) and K2CO3 (253 mg, 1.83 mmol), was added MeI (354 mg, 2.49 mmol) at room temperature and the reaction mix was stirred for 24 h at room temperature. The reaction mix was poured into water and extracted with ethyl acetate. The organic layer was separated, washed with water, dried and concentrated to give 2-cyano-5-methoxy pyridine (175 mg, 78% yield).

Workup

  1. additionthe reaction mix
  2. additionThe reaction mix
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3cbbf9f90d6f46cc8e82980c6ceb514b
Source dataset
uspto-grants-2013_04
Patent number
US08410109B2

Reaction notes

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