4-Propylaniline → HCID 67045729, compound

HRID 1023685Notes

Reaction equation

HRID 1023685 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[O:10][C:8](=O)[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2].[CH2:15]([C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)[CH2:16][CH3:17]>C(O)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:7](=[CH:13][CH:14]=1)[C:8](=[O:10])[N:22]([C:21]1[CH:23]=[CH:24][C:18]([CH2:15][CH2:16][CH3:17])=[CH:19][CH:20]=1)[C:11]2=[O:12])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 759084-PropylanilineHCID 2309764-Nitrophthalic acid anhydride

Product 1

HCID 67045729HCID 67045729, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 95% 4-nitrophthalic acid anhydride (4.22 g, 20.7 mmol) and 4-propylaniline (2.81 g, 20.7 mmol) in acetic acid (86 ml) was refluxed by heating for 24 hours. The reaction solution was cooled to room temperature, and then added to ice water, and the deposited crystals were collected by filtration, and washed with water. The resulting crystals were purified by recrystallization (ethanol) to obtain 5-nitro-2-(4-propyl-phenyl)-isoindole-1,3-dione as pale yellow scaly crystals (5.89 g, yield: 91.4%).

Workup

  1. temperatureby heating for 24 hours
  2. filtrationthe deposited crystals were collected by filtration
  3. washwashed with water
  4. customThe resulting crystals were purified by recrystallization (ethanol)

Sources & evidence

ORD record
ord-160258a1776d4a8c963291cbbf98c568
Source dataset
uspto-grants-2014_05
Patent number
US08722723B2

Reaction notes

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