Phthalic Anhydride → 2-[2-(4-Iodophenyl)ethyl]-1H-isoindole-1,3(2H)-dione

HRID 2250406Notes

Reaction equation

HRID 2250406 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.[C:11]1(=O)[O:16][C:14](=[O:15])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12>C(O)(=O)C>[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:14](=[O:15])[C:13]3[C:12](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:11]2=[O:16])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 151501452-(4-Iodophenyl)ethylamine

Product 1

HCID 685383782-[2-(4-Iodophenyl)ethyl]-1H-isoindole-1,3(2H)-dioneYield 64.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-(4-iodophenyl)ethylamine (7.08 g) and phthalic anhydride (4.24 g) in acetic acid (100 mL) was refluxed for 4 h. The solvent was evaporated and the residue triturated with ethanol (100 mL). The solid was filtered to afford the title intermediate (7.0 g) as a white solid.

Workup

  1. customThe solvent was evaporated
  2. customthe residue triturated with ethanol (100 mL)
  3. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-e20e5c2e08e344e5a72cc7bb57a90eb7
Source dataset
uspto-grants-2008_01
Patent number
US07317023B2

Reaction notes

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