(7-Bromo-3-nitroquinolin-4-yl)isobutylamine → 7-bromo-N4-isobutylquinoline-3,4-diamine

HRID 9452

Reaktionsgleichung

Reaktionsgleichung von HRID 9452
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[C:7]([N+:12]([O-])=O)[CH:8]=[N:9]2)=[CH:4][CH:3]=1>C(#N)C.C(O)(C)C.[Pt]>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[C:7]([NH2:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 1

HCID 21984282(7-Bromo-3-nitroquinolin-4-yl)isobutylamine

Produkt 1

HCID 688181597-bromo-N4-isobutylquinoline-3,4-diamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23939PlatinumKatalysatorHCID 3776IsopropanolLösungsmittel2×HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

A solution of (7-bromo-3-nitroquinolin-4-yl)-(2-methylpropyl)amine (30.9 g, 105 mmol) in acetonitrile (1.8 L) and isopropanol (200 mL) was added to a Parr vessel. A mixture of 5% platinum on carbon (3.0 g) and acetonitrile:isopropanol (20 mL) was added, and the vessel was purged with nitrogen. The vessel was placed under hydrogen pressure (40 psi, 2.8×105 Pa) for two hours. After one hour, the pressure had decreased to 20 psi (1.4×105 Pa) and was readjusted to 40 psi (2.8×105 Pa). The reaction mixture was filtered through a layer of CELITE filter aid, and the filter cake was washed with acetonitrile. The filtrate was concentrated under reduced pressure to provide 7-bromo-N4-(2-methylpropyl)quinoline-3,4-diamine as an oil.

Aufarbeitung

  1. customthe vessel was purged with nitrogen
  2. customfor two hours
  3. filtrationThe reaction mixture was filtered through a layer of CELITE
  4. filtrationfilter aid
  5. washthe filter cake was washed with acetonitrile
  6. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-aae0dad34e834b03a63c256ec63dadca
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091214B2

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