1-Bromopropane → 1-Chloro-6-propoxyisoquinoline

HRID 1852070노트

반응식

HRID 1852070 반응식
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.Br[CH2:14][CH2:15][CH3:16].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:14][CH2:15][CH3:16])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 1357421771-chloro-2H-isoquinolin-6-one

생성물 1

HCID 820629641-Chloro-6-propoxyisoquinoline수율 63.2%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of 1-chloroisoquinolin-6-ol (0.898 g, 5 mmol), 1-bromopropane (1.230 g, 10.00 mmol), and K2CO3 (2.073 g, 15.00 mmol) in acetone (20 mL) was refluxed for 16 h. The reaction mixture was filtrated and washed with acetone. the filtrate was concentrated and purified by silica gel chromatography eluting with 10-20% ethyl acetate in hexane to give 700 mg of the product 1-chloro-6-propoxyisoquinoline as a solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.27-8.16 (m, 2H), 7.48 (d, J=5.8 Hz, 1H), 7.31 (dd, J=9.3, 2.5 Hz, 1H), 7.09 (d, J=2.5 Hz, 1H), 4.09 (t, J=6.5 Hz, 2H), 2.02-1.84 (m, 2H), 1.11 (d, J=14.8 Hz, 1H); MS: MS m/z 222.16 (M++1).

후처리

  1. temperaturewas refluxed for 16 h
  2. filtrationThe reaction mixture was filtrated
  3. washwashed with acetone
  4. concentrationthe filtrate was concentrated
  5. custompurified by silica gel chromatography
  6. washeluting with 10-20% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-7b41564b6abe40eabaf91c079ac8d665
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957203B2

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