Isopropyl iodide → 1-Chloro-6-isopropoxyisoquinoline

HRID 1852071Notes

Reaction equation

HRID 1852071 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.I[CH:14]([CH3:16])[CH3:15].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][CH:14]([CH3:16])[CH3:15])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 1357421771-chloro-2H-isoquinolin-6-one

Product 1

HCID 534032981-Chloro-6-isopropoxyisoquinolineYield 58.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-chloroisoquinolin-6-ol (898 mg, 5 mmol), 2-iodopropane (1700 mg, 10.00 mmol), and K2CO3 (2073 mg, 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 650 mg of the product 1-chloro-6-isopropoxyisoquinoline as a solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.30-8.13 (m, 2H), 7.47 (d, J=5.3 Hz, 1H), 7.27 (d, J=2.5 Hz, 1H), 7.09 (d, J=2.5 Hz, 1H), 4.77 (dt, J=12.2, 6.1 Hz, 1H), 1.45 (d, J=6.0 Hz, 6H); 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-ebb56164d1fa453797f248ef909db8af
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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