N-cyclopentyl-3-nitropyridin-2-amine → N2-Cyclopentylpyridine-2,3-diamine
Reaction equation
[CH:1]1([NH:6][C:7]2[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([NH:6][C:7]2[C:12]([NH2:13])=[CH:11][CH:10]=[CH:9][N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of N-cyclopentyl-3-nitropyridin-2-amine (C4) (4.7 g, 23 mmol) in methanol (100 mL) was added palladium on carbon (0.5 g), and the mixture was degassed with hydrogen. After stirring under hydrogen at room temperature for 4 hours, the reaction mixture was filtered; the filtrate was concentrated in vacuo to afford the product as a black solid. Yield: 3.6 g, 20 mmol, 87%. 1H NMR (400 MHz, DMSO-d6) δ 7.35 (dd, J=5, 1 Hz, 1H), 6.63 (dd, J=7.3, 1.0 Hz, 1H), 6.30 (dd, J=7.3, 5.0 Hz, 1H), 5.31 (br d, J=6.3 Hz, 1H), 4.69 (br s, 2H), 4.18-4.28 (m, 1H), 1.88-2.00 (m, 2H), 1.61-1.75 (m, 2H), 1.36-1.60 (m, 4H).