2-Acetylamino-5-nitroquinoline → 2-Acetylamino-5-aminoquinoline

HRID 2215400Notes

Reaction equation

HRID 2215400 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N+:15]([O-])=O)[N:6]=1)(=[O:3])[CH3:2].[H][H]>C(OCC)(=O)C.CO.[Pd]>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH2:15])[N:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 219488732-Acetylamino-5-nitroquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 219488292-Acetylamino-5-aminoquinoline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

400 mg (1.7 mmol) of 2-acetylamino-5-nitroquinoline and 105 mg of 10% Pd—C are stirred in 20 ml of ethyl acetate-MeOH (3:1) for 4 hours in a hydrogen atmosphere at room temperature. The batch is filtered, concentrated by evaporation and purified by column chromatography on silica gel with hexane-ethyl acetate: 210 mg of product.

Workup

  1. filtrationThe batch is filtered
  2. concentrationconcentrated by evaporation
  3. custompurified by column chromatography on silica gel with hexane-ethyl acetate

Sources & evidence

ORD record
ord-4d1df30f3c5244ae9976f182bf3c359f
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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