6-(Benzyloxy)-3-nitropyridin-2-amine → 6-(Benzyloxy)pyridine-2,3-diamine
Reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]([NH2:15])[C:12]([N+:16]([O-])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC(O)=O.[Zn]>[CH2:1]([O:8][C:9]1[N:14]=[C:13]([NH2:15])[C:12]([NH2:16])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 6-(benzyloxy)-3-nitropyridin-2-amine (J. Med. Chem. 1997, 40, 1808) (22.67 g, 92.44 mmol) in AcOH (300 mL) was added zinc dust (24.18 g, 369.7 mmol) in four portions over 10 min while cooling in an ice bath. The mixture was then allowed to warm to room temperature and stirred for 2 h. The mixture was filtered and the solvent was removed under reduced pressure. The product was taken up in EtOAc and washed with saturated NaHCO3 solution and brine. The organics were dried over MgSO4, filtered and concentrated to yield the title compound as a black solid (19.31 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.13 (s, 2H), 5.14 (s, 2H), 5.39 (s, 2H), 5.86 (d, J=7.9 Hz, 1H), 6.77 (d, J=7.9 Hz, 1H), 7.28 (m, 1H), 7.34 (t, J=7.6 Hz, 2H), 7.40 (m, 2H).