2-benzyl-1,3(2H,4H)-isoquinolinedione → HCID 10377576, Verbindung

HRID 1378650Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1378650
[CH2:1]([N:8]1[C:17](=[O:18])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([N:8]1[CH:17]([OH:18])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 2725142-benzyl-1,3(2H,4H)-isoquinolinedioneHCID 4311764Sodium borohydride

Produkt 1

HCID 10377576HCID 10377576, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a well-stirred ice-bath-chilled solution of 2-benzyl-4H-isoquinoline-1,3-dione (5.0 g, 20 mmol) in methanol (40 ml), sodium borohydride (3.0 g, 80 mmol) was added portionwise over 20 minutes. The reaction mixture was stirred at ambient temperature for 48 hours. TLC inspection of a reaction aliquot confirmed substantial formation of product, with some starting material remaining. TLC Rf of the title compound (silica gel plates; u.v. detection; elution with ethyl acetate/hexane=3.7 in volume): 0.24. The ice-bath-chilled reaction mixture was cautiously quenched with water (3 ml). Anhydrous sodium sulfate was added to dry the mixture, which was then filtered. The filtrate was concentrated in vacuo to a dark green oil (3.5 g). Flash chromatography (silica gel, 40 micron mesh; elution with ethyl acetate hexane=3.7 volume) afforded the title compound as a colorless amorphous solid (1.35 g). The labile material was used immediately in the next step.

Aufarbeitung

  1. additionwas added portionwise over 20 minutes
  2. customTLC inspection of a reaction aliquot confirmed substantial formation of product

Quellen und Nachweise

ORD-Eintrag
ord-cff17a9040c94a78b64bda1258226bce
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05668145

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