Triethylamine → Ethyl 5-(3-nitroquinolin-4-ylamino)pentanoate

HRID 521330Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 521330
C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C.Cl.[NH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].Cl[C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=[CH:28][C:27]=1[N+:36]([O-:38])=[O:37]>C(Cl)(Cl)Cl.O>[N+:36]([C:27]1[CH:28]=[N:29][C:30]2[C:35]([C:26]=1[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:34][CH:33]=[CH:32][CH:31]=2)([O-:38])=[O:37]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 112758084-Chloro-3-nitroquinolineHCID 16094861Ethyl 5-aminopentanoate hydrochloride

Produkt 1

HCID 57447067Ethyl 5-(3-nitroquinolin-4-ylamino)pentanoateAusbeute 101,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Potassium carbonate (66.23 g, 0.479 mol), triethylamine (167 mL, 1.20 mol), and ethyl 5-aminovalerate hydrochloride (104 g, 0.575 mol) were added to a mixture of 4-chloro-3-nitroquinoline (100 g, 0.470 mol) in chloroform (1 L). The reaction mixture was stirred at room temperature for 4 hours, then water (200 mL) was added. The mixture was transferred to a separatory funnel and the layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 151 g of ethyl 5-[(3-nitroquinolin-4-yl)amino]pentanoate.

Aufarbeitung

  1. customThe mixture was transferred to a separatory funnel
  2. customthe layers were separated
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e60458ab254f403d93c3762e889c9ec1
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328110B2

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