Potassium Carbonate → Ethyl 5-(3-aminoquinolin-4-ylamino)pentanoate

HRID 2366680Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366680
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCl.O.CC[N+]1C=CC(C2C=C[N+](CC)=CC=2)=CC=1.[Br-].[Br-].S(S([O-])=O)([O-])=O.[Na+].[Na+]>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:11][CH:10]=[CH:9][CH:8]=2

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 57447067Ethyl 5-(3-nitroquinolin-4-ylamino)pentanoate

Produkt 1

HCID 57447068Ethyl 5-(3-aminoquinolin-4-ylamino)pentanoateAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24489Sodium DithioniteKatalysatorHCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of ethyl 5-(3-nitroquinolin-4-ylamino)pentanoate (151 g, 476 mmol) in dichloromethane (1 L) was added to a solution of sodium hydrosulfite (248.5 g, 1.427 mol), potassium carbonate (259.3 g, 1.876 mol), and ethyl viologen dibromide (1.78 g, 4.75 mmol) in water (1 L), and the reaction was stirred overnight at ambient temperature. An analysis by TLC indicated the presence of starting material; additional sodium hydrosulfite (5.0 g, 29 mmol) was added to the reaction, which was stirred for one additional hour. The organic layer was separated, washed with water (3×), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 131.51 g of ethyl 5-(3-aminoquinolin-4-ylamino)pentanoate.

Aufarbeitung

  1. stirringwas stirred for one additional hour
  2. customThe organic layer was separated
  3. washwashed with water (3×)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1c588760b1d44ee7a9d6bd225ab0afeb
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697873B2

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