Phthalic Anhydride → N-[3-(3,4-Dimethoxyphenyl)propyl]phthalimide

HRID 462113Notes

Reaction equation

HRID 462113 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][NH2:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:15]1(=O)[O:20][C:18](=[O:19])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][N:14]2[C:18](=[O:19])[C:17]3=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]3[C:15]2=[O:20])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 22810533,4-Dimethoxybenzenepropanamine

Product 1

HCID 21390569N-[3-(3,4-Dimethoxyphenyl)propyl]phthalimide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6.4 g of 3-(3,4-dimethoxyphenyl)-propylamine (0.03 moles) was refluxed with 5.47 g of phthalic anhydride (0.037 moles) in 70 ml of acetic acid for 2.5 hours. The solvent was then removed in the rotary evaporator. Recrystallization of the residue from 150 ml of ether gave 4.0 g of a first crop, m.p. 82°-85° and 7.0 g of a second crop, m.p. 81°-83°.

Workup

  1. customThe solvent was then removed in the rotary evaporator
  2. customRecrystallization of the residue from 150 ml of ether
  3. customgave 4.0 g of a first crop, m.p. 82°-85° and 7.0 g of a second crop, m.p. 81°-83°

Sources & evidence

ORD record
ord-2f7ce66a3b0841688bec7cca222ca4c8
Source dataset
uspto-grants-1977_12
Patent number
US04065473

Reaction notes

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