Water → HCID 2829574, compound

HRID 1730641Notes

Reaction equation

HRID 1730641 reaction equation
[CH:1]12[CH:14]=[CH:13][CH:5]([CH:6]3[C:11](=[O:12])O[C:8](=[O:9])[CH:7]31)[CH:4]1[CH:2]2[CH2:3]1.[N+:15]([C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)([O-:17])=[O:16].O>C(O)(=O)C>[N+:15]([C:18]1[CH:24]=[CH:23][C:21]([N:22]2[C:8](=[O:9])[CH:7]3[CH:6]([CH:5]4[CH:13]=[CH:14][CH:1]3[CH:2]3[CH:4]4[CH2:3]3)[C:11]2=[O:12])=[CH:20][CH:19]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 74754-NitroanilineHCID 2600324,4A,5,5a,6,6a-hexahydro-1H-4,6-ethenocyclopropa[f]isobenzofuran-1,3(3aH)-dione

Product 1

HCID 2829574HCID 2829574, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

250 g of tricyclo-[3.2.2.02.4 ]-non-8-ene-6,7-dicarboxylic acid anhydride (prepared from cycloheptatriene and maleic acid anhydride, K. Alder, Ber. 86, 1528-39 (1953)) and 200 g of 4-nitroaniline are refluxed in 1500 ml of glacial acetic acid for 3 hours. The reaction mixture cooled to 60° C is poured into 2000 ml of hot water, whereupon the crude product precipitates. After cooling, the crude product is filtered off, dried, and recrystallised from ethyl acetate; M.P. 210°-212° C.

Workup

  1. customprecipitates
  2. temperatureAfter cooling
  3. filtrationthe crude product is filtered off
  4. customdried
  5. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-46dfa1e78fbf46af9e465327256b6a8f
Source dataset
uspto-grants-1976_11
Patent number
US03993662

Reaction notes

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