Dimethylformamide → 2-(3-Tert-butyl-phenoxy)-3-methyl-5-nitro-pyridine

HRID 1894648Notes

Reaction equation

CN(C=O)C.[C:6]([C:10]1[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1)([CH3:9])([CH3:8])[CH3:7].Cl[C:18]1[C:23]([CH3:24])=[CH:22][C:21]([N+:25]([O-:27])=[O:26])=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+]>O>[C:6]([C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=1)[O:16][C:18]1[C:23]([CH3:24])=[CH:22][C:21]([N+:25]([O-:27])=[O:26])=[CH:20][N:19]=1)([CH3:9])([CH3:7])[CH3:8]

Participants

Conditions

Temperature: 60 °C

Procedure

A 50 ml two-necked round-bottomed flask equipped with a magnetic bar, a thermometer and a reflux condenser is charged with DMF (50 ml), 3-tert-butyl-phenol (1.5 g), 2-chloro-3-methyl-5-nitro-pyridine (1.73 g) and potassium carbonate (2.76 g). The reaction mixture is heated at 60° C. for 2 hours. After cooling the mixture to room temperature it is then poured into water (200 ml). The mixture is then extracted with ethylacetate (2×40 ml). The combined organic layers are dried over sodium sulfate, filtered and the solvent is removed in vacuo. Purification of this crude material by flash chromatography over silica gel with hexane/ethyl acetate 4:1 (v:v) gives 2.55 g of the compound as a yellow oil.

Workup

customA 50 ml two-necked round-bottomed flask equipped with a magnetic bar
temperatureAfter cooling the mixture to room temperature it
extractionThe mixture is then extracted with ethylacetate (2×40 ml)
dry with materialThe combined organic layers are dried over sodium sulfate
filtrationfiltered
customthe solvent is removed in vacuo
customPurification of this crude material by flash chromatography over silica gel with hexane/ethyl acetate 4:1 (v:v)

Sources & evidence

ORD record: ord-fd105cae3de44c62b1f33902c9310d15
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513286B2

Reaction notes

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