Hydrazine hydrate (1:1) → 8-Amino-7-(methylamino)quinoline
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]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- customThe catalyst was removed by filtration
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-e2d6092f1f964319a6cd5877d7dfe00c
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765760B2
Reaction notes
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