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

HRID 1376230Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1376230
[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-e4f337735cf54987bddfb57fcca78c56
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07169926B1

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