4-Methylamino-3-nitroquinoline → HCID 13958346, compound

HRID 580524Notes

Reaction equation

HRID 580524 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]=2

Participants

4

Reactant 1

HCID 139583214-Methylamino-3-nitroquinoline

Product 1

HCID 13958346HCID 13958346, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

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

  1. customAfter hydrogen absorption
  2. customthe catalyst is removed by filtration
  3. concentrationthe filtrate is concentrated in vacuo
  4. customThe residue is purified by column chromatography on silica gel
  5. 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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