Hydrazine hydrate (1:1) → N~7~-Methylquinoline-7,8-diamine

HRID 1772001Notes

Reaction equation

HRID 1772001 reaction equation
[CH3:1][NH:2][C:3]1[C:12]([N+:13]([O-])=O)=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.O.NN>CO.[Ni]>[CH3:1][NH:2][C:3]1[C:12]([NH2:13])=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 29985233N-Methyl-8-nitroquinolin-7-amine

Product 1

HCID 29971707N~7~-Methylquinoline-7,8-diamineYield 87.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-methyl-8-nitroquinolin-7-amine (1.6 g, 7.9 mmol) in MeOH (25 mL) was added hydrazine hydrate (2.25 g, 455 mmol) and Raney Ni (8 drops). The mixture was stirred at room temperature for 20 minutes. The catalyst was removed by filtration and the filtrate was concentrated to give N7-methylquinoline-7,8-diamine as a yellow solid (1.2 g, yield 80%). ESI MS: m/z 174 [M+H]+.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2cab1ecb9ed145beae261eae632eb5f5
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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