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

HRID 41409

Reaktionsgleichung

Reaktionsgleichung von HRID 41409
[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-3204a4b7bfac4724a29b02172a4d9b12
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530469B2

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