Potassium Carbonate → 5-(3-Chloropropoxy)-3,4-dihydroisoquinolin-1(2H)-one

HRID 1645915Notes

Reaction equation

HRID 1645915 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][C:7]2=[O:12].C(=O)([O-])[O-].[K+].[K+].Br[CH:20](O)[CH2:21][CH2:22][Cl:23]>C(O)C>[Cl:23][CH2:22][CH2:21][CH2:20][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][C:7]2=[O:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5211811-Bromo-3-chloropropanolHCID 132366635-Hydroxy-1,2,3,4-tetrahydroisoquinolin-1-one

Product 1

HCID 110755405-(3-Chloropropoxy)-3,4-dihydroisoquinolin-1(2H)-oneYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.0 g (22.0 mmol) of 3,4-dihydro-5-hydroxy-1(2H)-isoquinolinone and 6.7 g (48.5 mmol) of potassium carbonate in 100 ml of ethanol was refluxed for one hour. Then 10.9 ml (100 mmol) of 1-bromo-3-chloropropanol was added and refluxing continued for five hours. The solution was cooled and concentrated. The residue was dissolved in chloroform, filtered and concentrated to provide 4.45 g (85%) of 5-(3-chloropropoxy)-3,4-dihydro-1(2H)-isoquinolinone; mp 131.5°-133°.

Workup

  1. temperaturewas refluxed for one hour
  2. temperaturerefluxing
  3. temperatureThe solution was cooled
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in chloroform
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-accde32d9c4949798d5e09d51d18ad03
Source dataset
uspto-grants-1993_01
Patent number
US05177075

Reaction notes

Loading…