2-Methyl-5-nitroquinoline → 5-Quinolinamine, 2-methyl-
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]2Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- washwashed with ethyl acetate
- concentrationThe combined filtrates are concentrated by evaporation
Sources & evidence
- ORD record
- ord-95a717b61b4a425e9911bd9ad99529df
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07417056B2
Reaction notes
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