3-Nitroaniline → 3,3-Dimethyl-1-(3-nitrophenyl)pyrrolidine-2,5-dione

HRID 435043Notes

Reaction equation

HRID 435043 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].[CH3:11][C:12]([CH3:20])([CH2:16][C:17](O)=[O:18])[C:13](O)=[O:14]>C1(C)C(C)=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([N:7]2[C:17](=[O:18])[CH2:16][C:12]([CH3:20])([CH3:11])[C:13]2=[O:14])[CH:8]=[CH:9][CH:10]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 74233-NitroanilineHCID 117012,2-Dimethylsuccinic acid

Product 1

HCID 131892133,3-Dimethyl-1-(3-nitrophenyl)pyrrolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Sixty-nine grams (0.5 mole) of m-nitroaniline and 76 grams (g.) (0.52 mole) of 2,2-dimethylsuccinic acid were mixed with 200 milliliters (ml.) of xylene and heated to reflux until approximately 20 ml. of water was removed in a modified Dean Stark apparatus. On cooling, the product crystallized from solution. The mixture was diluted with 300 ml. of ether, the solid filtered off, washed with an additional 100 ml. of ether and dried. Yield was 117.5 g. of a product having a melting point (m.p.) of 134°-134.5° C. The product was identified as the title compound by analysis of infrared spectra.

Workup

  1. temperatureheated
  2. temperatureto reflux until approximately 20 ml
  3. customof water was removed in a modified Dean Stark apparatus
  4. temperatureOn cooling
  5. customthe product crystallized from solution
  6. additionThe mixture was diluted with 300 ml
  7. filtrationof ether, the solid filtered off
  8. washwashed with an additional 100 ml
  9. dry with materialof ether and dried
  10. customa melting point (m.p.) of 134°-134.5° C

Sources & evidence

ORD record
ord-8ba9e68e35b0463a81de96cfa51d8b02
Source dataset
uspto-grants-1983_08
Patent number
US04400202

Reaction notes

Loading…