2-Methyl-5-nitroquinoline → 5-Quinolinamine, 2-methyl-

HRID 2220239

Reaction equation

HRID 2220239 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N+:12]([O-])=O)[N:3]=1.[H][H]>[Pd].C(O)(=O)C>[NH2:12][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2]([CH3:1])=[N:3]2

Participants

5

Reactant 2

HCID 2948672-Methyl-5-nitroquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 1486835-Quinolinamine, 2-methyl-Yield 50.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

2-Methyl-5-nitroquinoline (25 g, 132.85 mmol) and palladium on carbon (2.5 g) in 8 ml of glacial acetic acid are stirred for 5½ hours in a hydrogen atmosphere at normal pressure. The catalyst is suctioned off and washed with ethyl acetate. The combined filtrates are concentrated by evaporation. Column chromatography of the residue on silica gel with dichloromethane-acetone yields 10.6 g of the product.

Workup

  1. washwashed with ethyl acetate
  2. concentrationThe combined filtrates are concentrated by evaporation

Sources & evidence

ORD record
ord-95a717b61b4a425e9911bd9ad99529df
Source dataset
uspto-grants-2008_08
Patent number
US07417056B2

Linked notes

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