1-Bromopropane → 1-Chloro-6-propoxyisoquinoline

HRID 1852070ノート

反応式

HRID 1852070 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 820629641-Chloro-6-propoxyisoquinoline収率 63.2%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7b41564b6abe40eabaf91c079ac8d665
出典データセット
uspto-grants-2015_02
特許番号
US08957203B2

反応ノート

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