Sodium Dithionite → 7-bromo-N4-isobutylquinoline-3,4-diamine

HRID 9349

Reaktionsgleichung

Reaktionsgleichung von HRID 9349
[O-]S(S([O-])=O)=O.[Na+].[Na+].[Br:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:23][CH2:24][CH:25]([CH3:27])[CH3:26])=[C:15]([N+:20]([O-])=O)[CH:16]=[N:17]2)=[CH:12][CH:11]=1>O.C(O)(C)C>[Br:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:23][CH2:24][CH:25]([CH3:27])[CH3:26])=[C:15]([NH2:20])[CH:16]=[N:17]2)=[CH:12][CH:11]=1

Komponenten

5

Edukt 2

HCID 24489Sodium DithioniteHCID 21984282(7-Bromo-3-nitroquinolin-4-yl)isobutylamine

Produkt 1

HCID 688181597-bromo-N4-isobutylquinoline-3,4-diamineAusbeute 135,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A solution of Na2S2O4 (193 g) in H2O (1 L) was added to a boiling solution of (7-bromo-3-nitroquinolin-4-yl)isobutylamine (32.0 g, 99 mmol) in isopropanol (1 L). Upon complete addition, the reaction mixture was cooled to room temperature and the bulk of the isopropanol was removed on a rotary evaporator. The resulting mixture was extracted with CH2Cl2 (3×), and the combined organic layers were dried over Na2SO4, filtered, and concentrated to afford 39.5 g of the crude 7-bromo-N4-isobutylquinoline-3,4-diamine as a yellow solid.

Aufarbeitung

  1. additionUpon complete addition
  2. customthe bulk of the isopropanol was removed on a rotary evaporator
  3. extractionThe resulting mixture was extracted with CH2Cl2 (3×)
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-630f53709a7641e4abb79b3ac6370174
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091214B2

Verknüpfte Notizen

Wird geladen…