Acetic Acid → N-(3-Hydroxy-4-chlorophenyl)-3,4,5,6-tetrahydrophthalimide

HRID 1578222Notes

Reaction equation

HRID 1578222 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2[CH2:7][CH2:8][CH2:9][CH2:10][C:2]1=2.[OH:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=1[Cl:20])[NH2:16].C(O)(=O)C>O>[Cl:20][C:19]1[CH:18]=[CH:17][C:15]([N:16]2[C:1](=[O:11])[C:2]3[CH2:10][CH2:9][CH2:8][CH2:7][C:3]=3[C:4]2=[O:6])=[CH:14][C:13]=1[OH:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 806765-Amino-2-chlorophenol

Product 1

HCID 12769235N-(3-Hydroxy-4-chlorophenyl)-3,4,5,6-tetrahydrophthalimideYield 87.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 15.2 g. of 3,4,5,6-tetrahydrophthalic anhydride, 14.4 g. of 3-hydroxy-4-chloroaniline and 50 ml. of glacial acetic acid was refluxed with stirring for 2 hours and then, the reaction mixture was cooled to a room temperature and water was added to precipitate a crystal and the crystal was separated by a filtration and recrystallized from isopropanol to obtain N-(4-chloro-3-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide (m.p.: 236.5°-238° C.; yellow crystal) (yield: 87.5%).

Workup

  1. additionA mixture of 15.2 g
  2. customto precipitate a crystal
  3. customthe crystal was separated by a filtration
  4. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-c65f39d531eb458e82de59d90ffac795
Source dataset
uspto-grants-1981_09
Patent number
US04292070

Reaction notes

Loading…