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

HRID 853797Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 853797
[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]

Komponenten

5

Edukt 3

HCID 4034-AminophenolHCID 962WaterHCID 118814-Hydroxyphthalic acid

Produkt 1

HCID 197939855-Hydroxy-2-(4-hydroxyphenyl)-1H-isoindole-1,3(2H)-dioneAusbeute 74,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

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+).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-8e8e4dc2f20a4b0b9f66723ccdbe3a00
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07256201B2

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