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

HRID 1378650노트

반응식

HRID 1378650 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 10377576HCID 10377576, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-cff17a9040c94a78b64bda1258226bce
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05668145

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