Toluene → HCID 178483721, Verbindung

HRID 18126

Reaktionsgleichung

Reaktionsgleichung von HRID 18126
[NH2:1][C:2]1[C:7]2=[CH:8][C:9]3[C:10]4[C:15]([C:14](=[O:16])[N:13]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[C:12](=[O:22])[C:11]=4[CH:23]=[CH:24][CH:25]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[OH:33][C:34]1[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][C:35]=1[CH:36]=O>C(Cl)Cl.CO>[OH:33][C:34]1[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][C:35]=1/[CH:36]=[N:1]\[C:2]1[C:7]2=[CH:8][C:9]3[C:10]4[C:15]([C:14](=[O:16])[N:13]([CH2:17][CH2:18][N:19]([CH3:20])[CH3:21])[C:12](=[O:22])[C:11]=4[CH:23]=[CH:24][CH:25]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 709492,5-DihydroxybenzaldehydeHCID 100654148-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione

Produkt 1

HCID 178483721HCID 178483721, VerbindungAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

A mixture of 50 mg (0.150 mmole) of 8-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione (obtained in example 4), 5 mL of toluene and 25 mg (1.2 molar equivalent) of 2,5-dihydroxybenzaldehyde was refluxed for 3 hours. After cooling, toluene was evaporated under reduced pressure and the residue was submitted to a flash chromatography on silica (eluent: CH2Cl2/methanol in a 95:5 and then a 90:10 volume ratio), thus resulting in 60 mg (yield: 88%) of the desired product (formula below) as a deep red powder.

Aufarbeitung

  1. temperaturewas refluxed for 3 hours
  2. temperatureAfter cooling
  3. customtoluene was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8082caa1a5ca4d7e9e3f980915bf164d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741337B2

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