N-Methyl-4-nitro-N-phenylbenzamide → 4-amino-N-methyl-N-phenylbenzamide

HRID 323125Notes

Reaction equation

[CH3:1][N:2]([C:9](=[O:19])[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(O)C.C(O)(=O)C.[Fe]>[CH3:1][N:2]([C:9](=[O:19])[C:10]1[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N-methyl-N-(4-nitrobenzoyl)aniline (1.18 g) and iron powder (2.57 g) in a mixture of ethanol (30 ml) and acetic acid (6 ml) was stirred at 80° C. for 3 hours and the mixture was cooled to ambient temperature. The mixture was filtered through Celite and the filtrate was evaporated in vacuo. The residue was dissolved in chloroform and neutralized with saturated aqueous sodium hydrogen carbonate. The solution was filtered through Celite again and the organic phase of the filtrate was washed with brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was solidified with diethyl ether to give N-methyl-N-(4-aminobenzoyl)aniline (754 mg) as a pale yellow solid.

Workup

temperaturethe mixture was cooled to ambient temperature
filtrationThe mixture was filtered through Celite
customthe filtrate was evaporated in vacuo
dissolutionThe residue was dissolved in chloroform and neutralized with saturated aqueous sodium hydrogen carbonate
filtrationThe solution was filtered through Celite again
washthe organic phase of the filtrate was washed with brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-fd3ae915da34461c8412275d406f9fcf
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211242B1

Reaction notes

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