Toluene → N-{4-[(Z)-2-(dimethylamino)ethenyl]-5-nitropyridin-2-yl}acetamide

HRID 875382

Reaction equation

[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=1.CO[CH:17](OC)[N:18]([CH3:20])[CH3:19].C1(C)C=CC=CC=1>CN(C)C=O>[CH3:17][N:18]([CH3:20])/[CH:19]=[CH:1]\[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of N-(4-methyl-5-nitropyridin-2-yl)acetamide (1 g, 5 mmol, Step a) in dry dimethylformamide (10 mL), dimethylformamide dimethyl acetal (1.5 mL, 11 mmol) was added and the resulting reaction mixture was heated at 90° C. for 3 hours. The reaction mixture was cooled to room temperature, toluene was added and evaporated under vacuum followed by triturating with diethyl ether and filtration to afford N-{4-[(Z)-2-(dimethylamino)ethenyl]-5-nitropyridin-2-yl}acetamide (0.8 g, 63%).

Workup

customthe resulting reaction mixture
temperatureThe reaction mixture was cooled to room temperature
customevaporated under vacuum
filtrationby triturating with diethyl ether and filtration

Sources & evidence

ORD record: ord-c6f74d2fc61043dca7ed5dad4296e326
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980911B2

Linked notes

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