4-Chloroquinoline → HCID 22935746, Verbindung

HRID 1352493Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1352493
[C:1]([N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=O)[CH2:11][CH:10]1[CH3:20])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([N:29]1C2C(=CC(Cl)=CC=2)C(=O)CC1C)(=O)[C:22]1C=CC=C[CH:23]=1.ClC1C2C(=CC=CC=2)N=CC=1.C(N)C#C>ClC(Cl)C.C1(C)C=CC=CC=1.[Cl-].[Ti+4].[Cl-].[Cl-].[Cl-].C(N(CC)CC)C>[CH3:20][CH:10]1[CH2:11][C:12](=[N:29][CH2:21][C:22]#[CH:23])[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]1[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8]

Komponenten

9

Edukt 4

HCID 691404-ChloroquinolineHCID 239041PropargylamineHCID 22935722HCID 22935722, VerbindungHCID 229357231-Benzoyl-2-methyl-2,3-dihydroquinolin-4(1H)-one

Produkt 1

HCID 22935746HCID 22935746, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 160960Diamminetetrachlorotitanate(IV)KatalysatorHCID 1140TolueneLösungsmittelHCID 63651,1-DichloroethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

To a solution of 1-benzoyl-2-methyl-2,3-dihydro-1H-quinolin-4-one (corresponds to a compound of general formula (3b) wherein R3 is phenyl, R4 is CH3 and R5, R6, R7, R8 are H, prepared as disclosed in example 46, according to protocol B, starting from 4-chloro-quinoline, (0.3 g), triethylamine (0.92 g), propargyl amine (0.125 g) in dichloroethane (20 ml), cooled at −5° C. in an ice/sodium chloride bath, a solution of titanium chloride in toluene 1 mol/l was dropwise added for 10 minutes. The mixture was stirred over night at room temperature and then washed with dichloromethane and an aqueous solution of potassium carbonate. The organic layer was separated, dried over sodium sulfate and the solvent was removed under reduced pressure to give (2-methyl-4-prop-2-ynylimino-3,4-dihydro-2H-quinolin-1-yl)-phenyl-methanone (brown oil) (0.5 g) which was not purified, but directly used in the next step

Aufarbeitung

  1. customprepared
  2. washwashed with dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-220a9c2554d34ab69b90083204b7b1ff
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07220760B2

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