Hydrochloric Acid → 1-(3-Aminophenyl)-3-ethyl-3-methylpyrrolidine-2,5-dione

HRID 435047

Reaction equation

HRID 435047 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:14](=[O:15])[CH2:13][C:12]([CH3:18])([CH2:16][CH3:17])[C:11]2=[O:19])[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl.C(O)C>[Fe].O>[NH2:1][C:4]1[CH:5]=[C:6]([N:10]2[C:14](=[O:15])[CH2:13][C:12]([CH3:18])([CH2:16][CH3:17])[C:11]2=[O:19])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 131892323-Ethyl-3-methyl-1-(3-nitrophenyl)pyrrolidine-2,5-dione

Product 1

HCID 131892171-(3-Aminophenyl)-3-ethyl-3-methylpyrrolidine-2,5-dione

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

Seventy-four g. of N-m-nitrophenyl-2-methyl-2-ethylsuccinimide, as prepared in Example VI, was added portion wise to 60 g. of iron powder, 4 ml. of concentrated HCl, 200 ml. of ethanol and 160 ml. of water at reflux. When addition was complete and the temperature had fallen to 70° C., the mixture was treated with 4 g. of 50% NaOH and filtered immediately. The filtercake was washed with hot ethyl alcohol and the filtrate stripped under vacuum. The product which crystallized on removal of the ethyl alcohol weighed 49 g. when dry and had a m.p. of 100°-102° C. The product was identified as the title compound by analysis of infrared spectra.

Workup

  1. additionwas added portion wise to 60 g
  2. additionWhen addition
  3. customhad fallen to 70° C.
  4. additionthe mixture was treated with 4 g
  5. filtrationof 50% NaOH and filtered immediately
  6. washThe filtercake was washed with hot ethyl alcohol
  7. customThe product which crystallized on removal of the ethyl alcohol
  8. customwhen dry

Sources & evidence

ORD record
ord-0da4dc040e1348cba3139d0453086179
Source dataset
uspto-grants-1983_08
Patent number
US04400202

Linked notes

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