1-Bromopropane → 1-Chloro-6-propoxyisoquinoline

HRID 1852070Notes

Reaction equation

HRID 1852070 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 820629641-Chloro-6-propoxyisoquinolineYield 63.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-7b41564b6abe40eabaf91c079ac8d665
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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