Ammonium Hydroxide → 2-(3,4-dimethoxyphenyl)pyridin-3-ol

HRID 2420092Notes

Reaction equation

HRID 2420092 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:6]([C:8]1[O:9][CH:10]=[CH:11][CH:12]=1)=O.[OH-].[NH4+:19]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[C:8]([OH:9])=[CH:12][CH:11]=[CH:10][N:19]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 8383262-(3,4-Dimethoxybenzoyl)furan

Product 1

HCID 43013592-(3,4-dimethoxyphenyl)pyridin-3-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(3,4-Dimethoxybenzoyl)furan (764.0 g, 3.28 moles, described in Example 2) is heated at 140° C in an autoclave in the presence of concentrated ammonium hydroxide (7 liters) and methanol (6 liters) for 17 hours. The mixture is cooled and concentrated to 4 liters. Methylene chloride (3 liters) is added and the mixture is extracted with 8N aqueous sodium hydroxide (500 ml). The aqueous extract is washed with methylene chloride. Ice is added to the aqueous phase followed by 6N hydrochloric acid to bring the pH between 7.5-7.0. The brown precipitate is collected, dried and milled to give the title compound, mp 150°-155° C.

Workup

  1. temperatureThe mixture is cooled
  2. concentrationconcentrated to 4 liters
  3. additionMethylene chloride (3 liters) is added
  4. extractionthe mixture is extracted with 8N aqueous sodium hydroxide (500 ml)
  5. extractionThe aqueous extract
  6. washis washed with methylene chloride
  7. additionIce is added to the aqueous phase
  8. customThe brown precipitate is collected
  9. customdried
  10. custommilled

Sources & evidence

ORD record
ord-93ba4bc8ea9f444aa6e77451e3d36491
Source dataset
uspto-grants-1978_08
Patent number
US04108997

Reaction notes

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