Potassium Carbonate → HCID 68874499, Verbindung

HRID 2366630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366630
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[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+]>CC[N+]1C=CC(C2C=C[N+](CC)=CC=2)=CC=1.[Br-].[Br-]>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=[CH:9][CH:8]=2

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 24489Sodium Dithionite2×HCID 68873567HCID 68873567, Verbindung

Produkt 1

HCID 68874499HCID 68874499, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromideKatalysator

Versuchsvorschrift

Ethyl N-(3-nitroquinolin-4-yl)-β-alaninate (41.6 g, 144 mmol, prepared as described in Part A of Example 15) was treated with sodium hydrosulfite (87.62 g, 503.3 mmol), potassium carbonate (78.5 g, 568 mmol), and ethyl viologen dibromide (0.54 g, 1.4 mmol) according to a modification of the method described in Part A of Example 8. After the reaction was stirred overnight, additional sodium hydrosulfite (5.0 g, 29 mmol) was added, and the reaction was stirred for one additional hour. The organic layer was separated, washed with water (5×200 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 33.3 g of ethyl N-(3-aminoquinolin-4-yl)-β-alaninate.

Aufarbeitung

  1. stirringthe reaction was stirred for one additional hour
  2. customThe organic layer was separated
  3. washwashed with water (5×200 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0821a5dc4e1448b6b1a9bf8301707a46
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697873B2

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