3-nitro-2-phenoxy-N-[2-(3-pyridin-3-ylpropoxy)ethyl]-5,6,7,8-tetrahydroquinolin-4-amine → 2-phenoxy-N4-[2-(3-pyridin-3-ylpropoxy)ethyl]-5,6,7,8-tetrahydroquinoline-3,4-diamine

HRID 432710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432710
[N+:1]([C:4]1[C:5]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:6][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[C:13]=1[NH:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)([O-])=O.[H][H]>C1(C)C=CC=CC=1.[Pt]>[O:27]([C:5]1[C:4]([NH2:1])=[C:13]([NH:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[N:6]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Komponenten

5

Edukt 2

HCID 187601773-nitro-2-phenoxy-N-[2-(3-pyridin-3-ylpropoxy)ethyl]-5,6,7,8-tetrahydroquinolin-4-amineHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 187601982-phenoxy-N4-[2-(3-pyridin-3-ylpropoxy)ethyl]-5,6,7,8-tetrahydroquinoline-3,4-diamineAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysator2×HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A 500 mL Parr bottle was charged with a solution of 3-nitro-2-phenoxy-N-[2-(3-pyridin-3-ylpropoxy)ethyl]-5,6,7,8-tetrahydroquinolin-4-amine in toluene (150 mL) and 5% Pt/C catalyst (1.1 g), placed on Parr apparatus and charged with hydrogen (˜54 psi, 3.8 Kg/cm2). The reaction was allowed to shake for 4 hours, at which time the reaction was monitored by HPLC. The reaction was not complete. An additional 1.0 g 5% Pt/C catalyst was added to the Parr bottle, it was recharged with hydrogen and shaken overnight. The reaction was then complete. The mixture was filtered through Celite and washed with toluene (500 mL). The filtrate was concentrated to provide 2-phenoxy-N4-[2-(3-pyridin-3-ylpropoxy)ethyl]-5,6,7,8-tetrahydroquinoline-3,4-diamine as a yellow syrup (8.2 g, 74%). TLC (10% MeOH/CH2Cl2, Rf=0.48). Mass-spec M+1=419.2

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with toluene (500 mL)
  3. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-e00cf6fe9a074888a18a88d83609c868
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06664260B2

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