Hydrochloric Acid → N-m-AMINOPHENYL-2,2-DIMETHYLSUCCINIMIDE

HRID 435044Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:14](=[O:15])[CH2:13][C:12]([CH3:17])([CH3:16])[C:11]2=[O:18])[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl.C(O)C.[OH-].[Na+]>[Fe].O>[NH2:1][C:4]1[CH:5]=[C:6]([N:10]2[C:14](=[O:15])[CH2:13][C:12]([CH3:16])([CH3:17])[C:11]2=[O:18])[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 70 °C

Procedure

One hundred and sixty three g. of N-m-nitrophenyl-2,2-dimethylsuccinimide, as prepared in Example I, was added portion wise at reflux temperature to a mixture of 115 g. of powdered iron, 7 ml. of concentrated HCl, 250 ml. of ethyl alcohol and 200 ml. of water. At completion of addition (approximately one hour), the mixture was allowed to cool to 70° C. and 7 g. of 50% sodium hydroxide was added and the iron oxide was removed by filtration through a Dicalite filter which was washed with several portions of hot ethyl alcohol. Stripping of the filtrate under vacuum yielded 106 g. of a product having a m.p. of 143°-145° C. A portion of the product was recrystallized to a m.p. of 147°-147.5° C. The product was identified as the title compound by analysis of infrared spectra.

Workup

additionwas added portion wise
temperatureat reflux temperature
additionto a mixture of 115 g
additionAt completion of addition (approximately one hour)
customthe iron oxide was removed by filtration through a Dicalite
filtrationfilter which
washwas washed with several portions of hot ethyl alcohol
customStripping of the filtrate under vacuum yielded 106 g
customA portion of the product was recrystallized to a m.p. of 147°-147.5° C

Sources & evidence

ORD record: ord-6d31c9f6b93f4252b99c8bcff903a24f
Source dataset: uspto-grants-1983_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04400202

Reaction notes

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