Acetic Acid → 4-Hydroxy-2-(4-methoxy-benzyl)-isoindole-1,3-dione

HRID 41408

Reaktionsgleichung

Reaktionsgleichung von HRID 41408
[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:4]2[C:5]([O:7][C:8](=[O:9])[C:3]=12)=O.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=1.C(O)(=O)C>O>[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:4]2[C:3]=1[C:8](=[O:9])[N:20]([CH2:19][C:18]1[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=1)[C:5]2=[O:7]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 754524-MethoxybenzylamineHCID 965803-Hydroxyphthalic anhydride

Produkt 1

HCID 592631454-Hydroxy-2-(4-methoxy-benzyl)-isoindole-1,3-dioneAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 3-hydroxyphthalic anhydride (543 mg, 3.31 mmol), 4-methoxybenzylamine (0.43 mL, 3.31 mmol) and acetic acid (3 mL) was heated at 100° C. for 4 hours. The mixture was allowed to cool and diluted with water (20 mL). The white solid was collected by filtration, washed well with water and dried to give the title compound (760 mg, 81%). 1H NMR (DMSO-d6) 11.03 (1H, s), 7.61 (1H, dd), 7.28 (1H, d), 7.23-7.19 (3H, m), 6.89-6.86 (2H, m), 4.63 (2H, s), 3.71 (3H, s). MS: [M−H+] 282.

Aufarbeitung

  1. temperatureto cool
  2. filtrationThe white solid was collected by filtration
  3. washwashed well with water
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-26a2cbfbb4d34563afa8982f03fdf0ef
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530469B2

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