Ammonia → 5,6,5'-Trimethyl-[2,2']bipyridin-3-ol

HRID 228823Notes

Reaction equation

HRID 228823 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12](C)[N:11]=2)=O)[O:5][C:6]=1[CH3:7].[NH3:17].[CH3:18]O>>[CH3:1][C:2]1[CH:3]=[C:4]([OH:5])[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:18])=[CH:12][N:11]=2)=[N:17][C:6]=1[CH3:7]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 23078390(4,5-Dimethylfuran-2-yl)-(6-methyl-pyridin-2-yl)methanone

Product 1

HCID 1363851085,6,5'-Trimethyl-[2,2']bipyridin-3-olYield 68%

Conditions

Temperature
160 °C

Procedure

(4,5-Dimethylfuran-2-yl)-(6-methyl-pyridin-2-yl)-methanone (780 mg), methanol (7 ml), and a 28% aqueous ammonia solution (7 ml) were placed in a sealed tube and were stirred at 160° C. overnight. 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 5,6,5′-trimethyl-[2,2′]bipyridin-3-ol (529 mg, yield 68%).

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-4bfe9740078f4312ab790b03d008545c
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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