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

HRID 344586Notes

Reaction equation

HRID 344586 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.[NH2:12][C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1>C(O)(=O)C>[OH:19][C:15]1[CH:14]=[C:13]([N:12]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:18]=[CH:17][CH:16]=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 25.0 g of 3,4,5,6-tetrahydrophthalic anhydride (THPA), 17.9 g of 3-aminophenol and 350 mL of glacial acetic acid was refluxed for 1 hour, then cooled and poured slowly into 1400 mL of ice-water. The resulting mixture was filtered, the collected solids were washed with cold water and dried (oven, reduced pressure) to give N-(3-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide (1A), as yellow crystals, m.p.: 196°-197.5° C.

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperaturecooled
  3. filtrationThe resulting mixture was filtered
  4. washthe collected solids were washed with cold water
  5. customdried (oven, reduced pressure)

Sources & evidence

ORD record
ord-e9e753f532b84feea632d06f1e9672f4
Source dataset
uspto-grants-1991_10
Patent number
US05053071

Reaction notes

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