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

HRID 2244818Notes

Reaction equation

HRID 2244818 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cb8eafc70f8e4568a94fbeaddcd990d9
Source dataset
uspto-grants-2010_03
Patent number
US07678909B1

Reaction notes

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