Ammonia → 5,6,4'-Trimethyl-[2,2']bipyridin-3-ol

HRID 228827Notes

Reaction equation

HRID 228827 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]=[C:14]([CH3:18])[CH:13]=[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 1363851095,6,4'-Trimethyl-[2,2']bipyridin-3-olYield 89%

Conditions

Temperature
160 °C

Procedure

(4,5-Dimethylfuran-2-yl)-(6-methyl-pyridin-2-yl)methanone (690 mg), methanol (6 ml), and a 28% aqueous ammonia solution (6 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 5,6,4′-trimethyl-[2,2′]bipyridin-3-ol (611 mg, yield 89%).

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-ffd4a15f6a86486c83f7b89c67a00ce8
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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