Toluene → 4-[2-(2,3-Dihydro-5,6-dimethoxy-1H-isoindol-2-yl)ethyl]benzenamine

HRID 1451649Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1451649
Cl[CH2:2][C:3]1[CH:4]=[C:5]([O:13][CH3:14])[C:6]([O:11][CH3:12])=[CH:7][C:8]=1[CH2:9]Cl.[OH-].[Na+].C1(C)C=CC=CC=1.[NH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][NH2:33])=[CH:27][CH:26]=1>O>[CH3:14][O:13][C:5]1[CH:4]=[C:3]2[C:8](=[CH:7][C:6]=1[O:11][CH3:12])[CH2:9][N:33]([CH2:32][CH2:31][C:28]1[CH:29]=[CH:30][C:25]([NH2:24])=[CH:26][CH:27]=1)[CH2:2]2

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 728952-(4-Aminophenyl)ethylamineHCID 109444001,2-Bis(chloromethyl)-4,5-dimethoxybenzene

Produkt 1

HCID 199745564-[2-(2,3-Dihydro-5,6-dimethoxy-1H-isoindol-2-yl)ethyl]benzenamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

4,5-Bischloromethyl veratrol (2.35 g: S. H. Wood, M. A. Peny and C. C. Tung, J. A. C. S. (1950), 72, 2989-2991) was added at room temperature to a stirred suspension of 50% aqueous sodium hydroxide (5 ml), toluene (25 ml), 4-aminophenylethylamine (1.5 g) and Aliquat (0.2 g). The heterogeneous mixture was stirred at room temperature for 16 hours, poured in water and extracted with methylene chloride. The organic layer was dried and the solvent evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with methylene dichloride/methanol (95:5) to give the title compound as a solid (0.6 g), MP: 150°. NMR includes signals at d 2.7(4H,m,Ph--CH2 --CH2 --N); 4.6(2H,bs,NH2); 3.7(6H,s,2×OCH3); 3.8(4H,s,2×N--CH2Ph); 6.2-7.0(6H,m,aromatics).

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. customThe organic layer was dried
  3. customthe solvent evaporated in vacuo
  4. customThe residue was purified by column chromatography on silica gel eluting with methylene dichloride/methanol (95:5)

Quellen und Nachweise

ORD-Eintrag
ord-bc39019733d845728ef69ee9952ea420
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05604237

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