Methanol → HCID 67300137, compound

HRID 2368216Notes

Reaction equation

HRID 2368216 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-636dc59aa50f4e54961dc69ff84135f1
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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