4-Chloro-8-methoxy-2-methylquinoline → (rac)-1-(4-Chlorophenyl)-N*1*-(8-methoxy-2-methylquinolin-4-yl)-N*2*,N*2*-dimethylethane-1,2-diamine dihydrochloride

HRID 1966537

Reaktionsgleichung

Reaktionsgleichung von HRID 1966537
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:14])[CH:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([NH2:27])[CH2:23][N:24]([CH3:26])[CH3:25])=[CH:18][CH:17]=1>C(OCC)(=O)C>[ClH:1].[ClH:15].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([CH:22]([NH:27][C:2]2[C:11]3[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([CH3:14])[CH:3]=2)[CH2:23][N:24]([CH3:25])[CH3:26])=[CH:20][CH:21]=1

Komponenten

4

Edukt 2

HCID 8075834-Chloro-8-methoxy-2-methylquinolineHCID 16643575(2-Amino-2-(4-chlorophenyl)ethyl)dimethylamine

Produkt 1

HCID 131730511(rac)-1-(4-Chlorophenyl)-N*1*-(8-methoxy-2-methylquinolin-4-yl)-N*2*,N*2*-dimethylethane-1,2-diamine dihydrochlorideAusbeute 60,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-Chloro-8-methoxy-2-methylquinoline (2.00 g, 9.63 mmole), 1-(4-chlorophenyl)N*2*,N*2*-dimethylethane-1,2-diamine (2.30 g, 11.6 mmole), sodium tert-butylate (1.3 g, 13.5 mmole), tris(dibenzylidenaceton)-dipalladium(0) (0.18 g, 0.193 mmole) and 2-dicyclohexyl-phosphino-2(N,N-dimethylamino)biphenyl (0.27 g, 0.674 mmole) were stirred at 150° C. under nitrogen atmosphere in a microwave oven for 30 min. The reaction mixture was dissolved in ethyl acetate and filtered. The filtrate was extracted with water. The organic phases were dried, concentrated and the residue was purified using silica gel chromatography, eluting with dichloromethane:methanol 90:10. Precipitation in isopropanol/HCl and in ethyl acetate gave the product (1.55 g, 36%).

Aufarbeitung

  1. filtrationfiltered
  2. extractionThe filtrate was extracted with water
  3. customThe organic phases were dried
  4. concentrationconcentrated
  5. customthe residue was purified
  6. washeluting with dichloromethane:methanol 90:10
  7. customPrecipitation in isopropanol/HCl

Quellen und Nachweise

ORD-Eintrag
ord-12c7456afd1f4763b019a5b648c41308
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420670B2

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