Sodium borohydride → 5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-ol

HRID 341828노트

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HRID 341828 반응식
[C:1]1([CH2:7][CH2:8][C:9]2[N:19]3[C:20]4[C:15]([C:16](=[O:21])[CH2:17][CH2:18]3)=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[C:1]1([CH2:7][CH2:8][C:9]2[N:19]3[C:20]4[C:15]([CH:16]([OH:21])[CH2:17][CH2:18]3)=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 158384624,5-dihydro-2-(2-phenylethyl)-6H-imidazo[4,5,1-ij]-quinolin-6-one

생성물 1

HCID 98604535,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-ol수율 94.3%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Fourteen grams of 4,5-dihydro-2-(2-phenylethyl)-6H-imidazo[4,5,1-ij]quinolin-6-one obtained in Example 1 was dissolved in dry methanol (140 mL); following the addition of sodium borohydride (0.76 g) under ice cooling and subsequent stirring at room temperature for 1 hr, the solvent was removed under reduced pressure and water was added to the residue, followed by extraction with dichloromethane. The organic layers were combined, washed with water and saturated brine successively, and dried over anhydrous sodium sulfate; thereafter, the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluting solution: hexane/ethyl acetate) to yield the titled compound as colorless crystals (13.3 g).

후처리

  1. customthe solvent was removed under reduced pressure and water
  2. additionwas added to the residue
  3. extractionfollowed by extraction with dichloromethane
  4. washwashed with water and saturated brine successively
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthereafter, the solvent was removed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluting solution: hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-bbf2ba647b7b43ccb5f88d4e884f9a88
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856334

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