4-Aminophenol → 5-Hydroxy-2-(4-hydroxyphenyl)-1H-isoindole-1,3(2H)-dione

HRID 853797Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=O)[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=O.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.O>C(O)(=O)C>[OH:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:9][CH:10]=1)[C:6](=[O:8])[N:14]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[C:11]2=[O:13]

Participants

Conditions

Temperature: 120 °C

Procedure

A suspension of 4-hydroxyphthalic acid (3.00 g) and 4-aminophenol (1.98 g) in glacial acetic acid (15 mL) was heated under nitrogen at 120° C. for 1.5 h. The brown reaction solution was cooled to room temperature, poured into water (200 mL) and allowed to sit undisturbed for 30 min. The precipitate was collected by filtration and washed with water (2×60 mL). The solid was dried under high vacuum at 50° C. for 18 h yielding the title compound (3.14 g) as a tan solid. 1H NMR (DMSO-d6): 10.99 (s, 1H), 9.72 (s, 1H), 7.76 (d, 1H, J=7.8 Hz), 7.18 (m, 4M), 6.86 (m, 2H); MS: 256 (MH+).

Workup

temperatureThe brown reaction solution was cooled to room temperature
filtrationThe precipitate was collected by filtration
washwashed with water (2×60 mL)
customThe solid was dried under high vacuum at 50° C. for 18 h

Sources & evidence

ORD record: ord-8e8e4dc2f20a4b0b9f66723ccdbe3a00
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07256201B2

Reaction notes

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