4-Methylamino-3-nitroquinoline → 3-Amino-4-(methylamino)quinoline
Reaction equation
[CH3:1][NH:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]=1[N+:13]([O-])=O>C(O)C.[Pd]>[NH2:13][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:3]=1[NH:2][CH3:1])=[CH:11][CH:10]=[CH:9][CH:8]=2Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A suspension of 1.7 g of 4-methylamino-3-nitroquinoline in 75 ml of ethanol is hydrogenated in the presence of 300 mg of 10% palladium on carbon at atmospheric pressure. After hydrogen absorption is complete, the catalyst is removed by filtration and the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel. Elution with chloroform-methanol (2:1 v/v) affords 600 mg (41%) of 3-amino-4-methylaminoquinoline A15 as an oil.
Workup
- customAfter hydrogen absorption
- customthe catalyst is removed by filtration
- concentrationthe filtrate is concentrated in vacuo
- customThe residue is purified by column chromatography on silica gel
- washElution with chloroform-methanol (2:1 v/v)
Sources & evidence
- ORD record
- ord-025ef8fb61934d759fc6cef98b1fbb90
- Source dataset
- uspto-grants-1988_06
- Patent number
- US04753951
Reaction notes
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