Ammonia → 5,6-Dimethyl-3-hydroxy-[2,3']bipyridine

HRID 228815Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=O)[O:5][C:6]=1[CH3:7].[NH3:16]>CO>[CH3:1][C:2]1[CH:3]=[C:4]([OH:5])[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[N:16][C:6]=1[CH3:7]

Participants

Conditions

Temperature: 160 °C

Procedure

(4,5-Dimethylfuran-2-yl)-(3-pyridyl)-methanone (1.8 g), methanol (30 ml), and a 28% aqueous ammonia solution (30 ml) were placed in a sealed tube and were stirred at 160° C. overnight. The reaction solution was cooled to room temperature, and the solvent was then removed by distillation under the reduced pressure. The residue was purified by column chromatography using hexane-ethyl acetate to give 5,6-dimethyl-[2,3′]-bipyridin-3-ol (1.1 g, yield 63%).

Workup

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

Sources & evidence

ORD record: ord-931cabd6e6414abf9158cfe60a3ab629
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Reaction notes

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