Methanol → HCID 67300137, compound

HRID 467619Notes

Reaction equation

HRID 467619 reaction equation
[Br:1][C:2]1[C:3]([C:11]#N)=[N:4][C:5]([CH2:8][O:9][CH3:10])=[CH:6][CH:7]=1.[OH-:13].[K+].C[OH:16]>O>[Br:1][C:2]1[C:3]([C:11]([OH:16])=[O:13])=[N:4][C:5]([CH2:8][O:9][CH3:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 67299906HCID 67299906, compound

Product 1

HCID 67300137HCID 67300137, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-bromo-6-methoxymethyl-pyridine-2-carbonitrile (300 mg, 1.32 mmol) in MeOH (6 ml) was added a solution of potassium hydroxide (1.48 g, 26.43 mmol) in water (4 ml). The mixture was refluxed for 3 hours. MeOH was removed in vacuo, the aqueous solution was neutralized with conc. HCl under cooling, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried, filtered and evaporated. The obtained product (276 mg, 85%) was used in the next step without any further purification.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. customMeOH was removed in vacuo
  3. temperatureunder cooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe combined organic layers were washed with water and brine
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe obtained product (276 mg, 85%) was used in the next step without any further purification

Sources & evidence

ORD record
ord-3aa9c0b6296c4f28bd3b9827fb385e6c
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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