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

HRID 1645915Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1645915
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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°.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-accde32d9c4949798d5e09d51d18ad03
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05177075

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