5-Chlorovaleryl chloride → HCID 66620499, Verbindung

HRID 415509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 415509
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[NH2:12].[Cl:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](Cl)=[O:19]>ClCCCl.ClCCl>[Cl:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([NH:12][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[Cl:1])=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:19]

Komponenten

5

Edukt 2

HCID 740895-Chlorovaleryl chloride2×HCID 8173324-chloroquinolin-3-amine

Produkt 1

HCID 66620499HCID 66620499, VerbindungAusbeute 56,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4-chloroquinolin-3-amine (4.00 g, 22.39 mmol) and 5-chlorovaleryl chloride (1.30 mL, 33.6 mmol) dissolved in 150 mL of 1,2-dichloroethane was heated to reflux. After 2.8 days more 5-chlorovaleryl chloride (1.0 mL, 7.7 mmol) was added. After 16 hours more the reaction was cooled to room temperature, diluted with dichloromethane, washed with saturated aqueous K2CO3, H2O, and brine, dried over Na2SO4, and concentrated under reduced pressure to give 3.78 g of 5-chloro-N-(4-chloroquinolin-3-yl)pentanamide as a tan solid.

Aufarbeitung

  1. temperaturewas heated to reflux
  2. washwashed with saturated aqueous K2CO3, H2O, and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ce5fc8b305d743da853db8069be0902b
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088788B2

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