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

HRID 229050Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][N:11]=2)=O)[O:5][C:6]=1[CH3:7].[NH3:17]>CO>[CH3:1][C:2]1[CH:3]=[C:4]([OH:5])[C:8]([C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][N:11]=2)=[N:17][C:6]=1[CH3:7]

Participants

Conditions

Temperature: 160 °C

Procedure

(4,5-Dimethylfuran-2-yl)-(3-methylpyridin-2-yl)-methanone (930 mg), methanol (7.5 ml), and a 28% aqueous ammonia solution (9 ml) were placed in a sealed tube and was 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, and the residue was purified by column chromatography using hexane-ethyl acetate to give 5,6,3′-trimethyl-[2,2′]bipyridin-3-ol (109 mg, yield 86%).

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-297816563b46479b908998063814036b
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Reaction notes

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