3-Aminophenol → 4,5,6,7-Tetrahydro-2-(3-hydroxyphenyl)-1H-isoindole-1,3(2H)-dione

HRID 1578223Notes

Reaction equation

HRID 1578223 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][CH:19]=1)[NH2:16]>C(O)(=O)C>[OH:12][C:13]1[CH:14]=[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:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 115683-AminophenolHCID 124753,4,5,6-Tetrahydrophthalic anhydride

Product 1

HCID 127692364,5,6,7-Tetrahydro-2-(3-hydroxyphenyl)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3,4,5,6-tetrahydrophthalic anhydride, 3-hydroxyaniline and a glacial acetic acid was heated to obtain N-(3-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide (m.p.: 199° to 201° C.) and 40.6 g. of the product was dissolved into 600 ml. of glacial acetic acid and 27.2 g. of bromine was added dropwise at 30° to 40° C. and the mixture was stirred at a room temperature for 5 hours to precipitate a crystal. The crystal was separated by a filtration and washed with methanol and recrystallized from benzene-tetrahydrofuran to obtain N-(4-bromo-3-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide (m.p.: 247°-248° C.; yellow crystal) (yield: 88%).

Sources & evidence

ORD record
ord-fcbec04a8aa940489dd95f17db97c54a
Source dataset
uspto-grants-1981_09
Patent number
US04292070

Reaction notes

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