Water → 5,6-dihydro-6-methoxy-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline

HRID 341839노트

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HRID 341839 반응식
[H-].[Na+].[C:3]1([CH2:9][CH2:10][C:11]2[N:21]3[C:22]4[C:17]([CH:18]([OH:23])[CH2:19][CH2:20]3)=[CH:16][CH:15]=[CH:14][C:13]=4[N:12]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:24]I.O>O1CCCC1>[CH3:24][O:23][CH:18]1[C:17]2[C:22]3=[C:13]([N:12]=[C:11]([CH2:10][CH2:9][C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=4)[N:21]3[CH2:20][CH2:19]1)[CH:14]=[CH:15][CH:16]=2

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 98604535,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-ol

생성물 1

HCID 158384685,6-dihydro-6-methoxy-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline수율 49%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A portion (115 mg) of 60% sodium hydride was added to anhydrous tetrahydrofuran (15 mL) under an argon atmosphere; 0.2 g of 5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-ol obtained in Example 4 was dissolved in anhydrous tetrahydrofuran (4 mL) and the solution was added dropwise to the first mentioned solution at room temperature. After stirring for 35 min at room temperature, methyl iodide (1.02 g) was added dropwise and the mixture was stirred for 4 hrs. Water was added to the reaction solution and the mixture was stirred; thereafter, the reaction solution was extracted with dichloromethane, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to yield the titled compound as a yellow oil (103 mg).

후처리

  1. additionthe solution was added dropwise to the
  2. customat room temperature
  3. stirringthe mixture was stirred for 4 hrs
  4. stirringthe mixture was stirred
  5. extractionthereafter, the reaction solution was extracted with dichloromethane
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-1cf4f09a45d64ca1861103abf45f5aa5
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856334

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