Water → 2-(2-Ethoxy-4-nitrophenyl)-1H-isoindole-1,3(2H)-dione

HRID 2290548Notes

Reaction equation

HRID 2290548 reaction equation
[CH2:1]([O:3][C:4]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=1[NH2:6])[CH3:2].[C:14]1(=O)[O:19][C:17](=[O:18])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.O>C(O)(=O)C>[CH2:1]([O:3][C:4]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=1[N:6]1[C:17](=[O:18])[C:16]2[C:15](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14]1=[O:19])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6811Phthalic AnhydrideHCID 853862-Ethyoxy-4-nitroaniline

Product 1

HCID 202314402-(2-Ethoxy-4-nitrophenyl)-1H-isoindole-1,3(2H)-dioneYield 83.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred mixture of 15.0 g (10.1 mole) of 2-ethoxy-4-nitroaniline and 13.4 g (0.09 mole) of phthalic anhydride in 100 ml of glacial acetic acid was heated at reflux for approximately 18 hours. The reaction mixture was cooled then poured into 700 ml of water to produce a solid which was collected by filtration. The solid was dissolved in methylene chloride, and the resultant solution washed first with an aqueous 10% potassium carbonate solution followed by an aqueous sodium chloride solution. The washed organic solution was dried over anhydrous sodium sulfate, filtered, and the filtrate evaporated under reduced pressure to yield 23.5 g of 2-(2-ethoxy-4-nitrophenyl)-1H-isoindol-1,3-(2H)-dione as a solid (mp 204°-206° C.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for approximately 18 hours
  3. temperatureThe reaction mixture was cooled
  4. customto produce a solid which
  5. filtrationwas collected by filtration
  6. dissolutionThe solid was dissolved in methylene chloride
  7. washthe resultant solution washed first with an aqueous 10% potassium carbonate solution
  8. dry with materialThe washed organic solution was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-1dcbd3848f5c4f4d8202a52cf8e084d9
Source dataset
uspto-grants-1986_10
Patent number
US04617316

Reaction notes

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