Ammonium Acetate → 5,6-Dimethyl-2-phenyl-pyridin-3-ol

HRID 228809

Reaction equation

HRID 228809 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)[O:5][C:6]=1[CH3:7].C([O-])(=O)C.[NH4+:20]>>[CH3:1][C:2]1[CH:3]=[C:4]([OH:5])[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:20][C:6]=1[CH3:7]

Participants

3

Reactant 2

HCID 517165Ammonium AcetateHCID 23078263(4,5-Dimethylfuran-2-yl)-phenyl-methanone

Product 1

HCID 230783805,6-Dimethyl-2-phenyl-pyridin-3-olYield 16,079.1%

Conditions

Temperature
250 °C

Procedure

(4,5-Dimethylfuran-2-yl)-phenyl-methanone (1 g) and ammonium acetate (910 mg) were placed in a sealed tube, and the mixture was stirred at 250° C. for 10 hr. The reaction solution was cooled to room temperature, the solvent was then removed by distillation under the reduced pressure, and the residue was purified by column chromatography using hexane-ethyl acetate to give 5,6-dimethyl-2-phenyl-pyridin-3-ol (160 g, yield 16%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. customthe solvent was then removed by distillation under the reduced pressure
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-09edd896e4074eec884e88b7cdbc2141
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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