6-Methyl-3-nitro-5,6,7,8-tetrahydro-1,6-naphthyridine → 3-Amino-5,6,7,8-tetrahydro-6-methyl-1,6-naphthyridine
Reaction equation
[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2[N:8]=[CH:7][C:6]([N+:12]([O-])=O)=[CH:5][C:4]=2[CH2:3]1>CO.[Pd]>[NH2:12][C:6]1[CH:7]=[N:8][C:9]2[CH2:10][CH2:11][N:2]([CH3:1])[CH2:3][C:4]=2[CH:5]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
6-Methyl-3-nitro-5,6,7,8-tetrahydro[1,6]naphthyridine (2.72 g, 1.41 mmol) was dissolved in methanol (100 ml) and treated with 10% palladium on carbon (1.0 g). The mixture was hydrogenated for 2 h. The catalyst was removed by filtration through Celite, the filter bed washed with methanol and the filtrate evaporated to dryness under reduced pressure to give a yellow solid, which was triturated under diethyl ether and the solids collected by filtration, washed with diethyl ether and dried in vacuo (1.89 g, 83%)