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

HRID 1378650Notes

Reaction equation

HRID 1378650 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 10377576HCID 10377576, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-cff17a9040c94a78b64bda1258226bce
Source dataset
uspto-grants-1997_09
Patent number
US05668145

Reaction notes

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