Acetic Acid → 2-(2,4-Dimethoxy-benzyl)-4-hydroxy-isoindole-1,3-dione

HRID 334908

Reaktionsgleichung

Reaktionsgleichung von HRID 334908
[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]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:16]=1[CH2:17][NH2:18].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:18]([CH2:17][C:16]1[CH:19]=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:15]=1[O:14][CH3:13])[C:5]2=[O:7]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 965803-Hydroxyphthalic anhydrideHCID 5972502,4-Dimethoxybenzylamine

Produkt 1

HCID 592631282-(2,4-Dimethoxy-benzyl)-4-hydroxy-isoindole-1,3-dioneAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 3-hydroxyphthalic anhydride (1.24 g, 7.6 mmol), 2,4-dimethoxybenzylamine (1.14 mL, 7.6 mmol) and acetic acid (5 mL) was heated at 80° C. for 24 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 (1.73 g, 73%). 1H NMR (DMSO-d6) 11.00 (1H, s), 7.62 (1H, dd), 7.29 (1H, d), 7.21 (1H, d), 6.90 (1H, d), 6.56 (1H, d), 6.43 (1H, dd), 4.59 (2H, s), 3.79 (3H, s), 3.72 (3H, s). MS: [M−H+] 314.

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-2bddb97b340e4acaa2e44fa5cb0bb63a
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883790B2

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