4-azido-1-methyl-3-nitro-1H-quinolin-2-one → 3,4-Diamino-1-methylquinolin-2(1H)-one

HRID 2244818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2244818
[N:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH3:14])[C:6](=[O:15])[C:5]=1[N+:16]([O-])=O)=[N+]=[N-]>CCO.[Pd]>[NH2:16][C:5]1[C:6](=[O:15])[N:7]([CH3:14])[C:8]2[C:13]([C:4]=1[NH2:1])=[CH:12][CH:11]=[CH:10][CH:9]=2

Komponenten

4

Edukt 1

HCID 3874734-azido-1-methyl-3-nitro-1H-quinolin-2-one

Produkt 1

HCID 451232943,4-Diamino-1-methylquinolin-2(1H)-oneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 4-azido-1-methyl-3-nitro-1H-quinolin-2-one (1.0 g, 4.08 mmol) in EtOH (40 mL) was hydrogenated at 1 atm over 10% Pd/C (0.781 g, 0.734 mmol) at room temperature. After 1 h, the reaction vessel was purged with nitrogen, and the catalyst was removed by filtration, rinsing with MeOH. The filtrate was concentrated in vacuo, to give 0.71 g (92%) of 3,4-diamino-1-methyl-1H-quinolin-2-one. 1H-NMR (DMSO): δ 7.82 (d, 1H, J=7.2 Hz), 7.39 (m, 2H), 7.19 (t, 1H, J=2.4 Hz), 5.48 (s, 2H), 4.35 (s, 2H), 3.63 (s, 3H). MS: calculated for C10H11N3O+H 190.1; found: 190.2.

Aufarbeitung

  1. customthe reaction vessel was purged with nitrogen
  2. customthe catalyst was removed by filtration
  3. washrinsing with MeOH
  4. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cb8eafc70f8e4568a94fbeaddcd990d9
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678909B1

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