Benzoyl chloride → 5-Benzoyloxyisoquinoline

HRID 31106

반응식

HRID 31106 반응식
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.C(N(CC)CC)C.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[C:19]([O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 30386Isoquinolin-5-ol

생성물 1

HCID 230773935-Benzoyloxyisoquinoline수율 103.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

To a solution of 5-hydroxyisoquinoline (15.0 g, 103 mmol) in dichloromethane (300 ml) was added triethylamine (10.9 g, 108 mmol), and the mixture was cooled to 0° C. Under stirring, benzoyl chloride (15.2 g, 108 mmol) was added dropwise and the temperature was raised to room temperature. After stirring for 6 hours at room temperature, dichloromethane was added. The solution was washed with saturated aqueous solution of sodium hydrogencarbonate, then dried over anhydrous magnesium sulfate and solvent was distilled off, thereby affording 26.6 g of the title compound as a light brown liquid. Yield quantitative. 1H-NMR (DMSO-d6, δ): 7.68(2H, t, J=7.3 Hz), 7.75(1H, d, J=5.9 Hz), 7.79-7.85(3H, m), 8.12-8.16(1H, m), 8.28(2H, d, J=7.3 Hz), 8.55 (1H, d, J=5.9 Hz), 9.45(1H, s).

후처리

  1. temperaturethe temperature was raised to room temperature
  2. stirringAfter stirring for 6 hours at room temperature
  3. washThe solution was washed with saturated aqueous solution of sodium hydrogencarbonate
  4. dry with materialdried over anhydrous magnesium sulfate and solvent
  5. distillationwas distilled off

출처 및 근거

ORD 기록
ord-21ef90c8a9bb49ffb7cad4f0e5118f94
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425563B2

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