Ammonia → 5,6-Dimethyl-2-(6-methylpyridin-2-yl)pyridin-3-ol

HRID 228819

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[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[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=2)=[N:17][C:6]=1[CH3:7]

Participants

Conditions

Temperature: 160 °C

Procedure

(4,5-Dimethylfuran-2-yl)-(6-methyl-pyridin-2-yl)-methanone (810 mg), methanol (7 ml), and a 28% aqueous ammonia solution (7 ml) were placed in a sealed tube, and the mixture was 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 5,6,6′-trimethyl-[2,2′]bipyridin-3-ol (753 mg, yield 93%).

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-a944364cd8f04728b8ddcf3d402af187
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Linked notes

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