4,7-Dichloroquinoline → 2-[2-(7-Chloroquinolin-4-ylamino)ethoxy]ethanol

HRID 550886Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 550886
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][OH:19]>C(OCC)C.ClCCl.C(N(CC)CC)C>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][OH:19])=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Komponenten

5

Edukt 2

HCID 68664,7-DichloroquinolineHCID 13578Diglycolamine

Produkt 1

HCID 533604522-[2-(7-Chloroquinolin-4-ylamino)ethoxy]ethanolAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 21882572Triethylamine methylene chlorideLösungsmittel

Versuchsvorschrift

A mixture of 4,7-dichloroquinoline (5.0 g, 25.0 mmol) and of 2-(2-aminoethoxy)ethanol (10.51 g, 100.0 mmol) is heated at 135° C. for 5 h, with magnetic stirring. After cooling, the reaction medium is taken up in 200 ml of diethyl ether and the stirring is maintained overnight at ambient temperature. The solid residue formed is isolated, and then dissolved in a mixture of 500 ml of dichloromethane/triethylamine (9/1, v/v) and filtered through sintered glass containing a bed of silica (SiO2 60 AAC 70-200 μm). The product is then eluted from the silica with ethanol (2 l). The ethanolic phases are combined and evaporated. 50 ml of dichloromethane are added to the residue and the organic phase is washed with twice 50 ml of water. The organic phase is recovered, dried over Na2SO4, and then evaporated in a rotary evaporator. After drying under vacuum, the compound 21 is obtained in the form of a beige powder: 5.03 g (yield=75%).

Aufarbeitung

  1. temperatureAfter cooling
  2. customThe solid residue formed
  3. customis isolated
  4. filtrationv/v) and filtered through sintered glass
  5. additioncontaining a bed of silica (SiO2 60 AAC 70-200 μm)
  6. washThe product is then eluted from the silica with ethanol (2 l)
  7. customevaporated
  8. addition50 ml of dichloromethane are added to the residue
  9. washthe organic phase is washed with twice 50 ml of water
  10. customThe organic phase is recovered
  11. dry with materialdried over Na2SO4
  12. customevaporated in a rotary evaporator
  13. customAfter drying under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0e3436206857486aa42eb2a9cb7ddecf
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947701B2

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