4-Methyl-5,6-dimethoxy-8-nitroquinoline → 8-Amino-5,6-dimethoxy-4-methylquinoline

HRID 1863113Notes

Reaction equation

HRID 1863113 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([N+:15]([O-])=O)=[C:9]2[C:4]=1[C:5]([CH3:18])=[CH:6][CH:7]=[N:8]2>[Ni]>[NH2:15][C:10]1[CH:11]=[C:12]([O:13][CH3:14])[C:3]([O:2][CH3:1])=[C:4]2[C:9]=1[N:8]=[CH:7][CH:6]=[C:5]2[CH3:18]

Participants

3

Reactant 1

HCID 6191084-Methyl-5,6-dimethoxy-8-nitroquinoline

Product 1

HCID 6090098-Amino-5,6-dimethoxy-4-methylquinolineYield 84%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

The nitro compound was reduced catalytically in ethanol-dioxane with use of Raney nickel. An 84% yield of 8-amino-5,6-dimethoxy-4-methylquinoline resulted. It could be crystallized from cyclohexane or from benzene-petroleum ether mixture; mp 108°-110° (softening at 103°).

Sources & evidence

ORD record
ord-ebead29cebfc45149c8d577afa90c8bc
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

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