1,5-Dimethyl-3-nitropyridin-2-one → 3-Amino-1,5-dimethyl-1,2-dihydropyridin-2-one
Reaction equation
[CH3:1][N:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([N+:9]([O-])=O)[C:3]1=[O:12]>CO.[Ni]>[NH2:9][C:4]1[C:3](=[O:12])[N:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 9.74 g (57.9 mmol) 1,5-dimethyl-3-nitropyridin-2(1H)-one (product from step 199.5), 2 g (57.9 mmol) Raney-Ni in 230 ml methanol was shaken in a duck glass under H2 atmosphere for 16 hours. After that, the mixture was filtered over celite, washed with MeOH, concentrated in vacuum and dried at high vacuum over night to obtain 7.9 g (57.2 mmol, 99% yield) of the title compound as a brownish solid. LCMS: (M+H)=139; tR=0.43 min (LC-MS 6). HPLC: tR=1.22 min (HPLC 8). 1H-NMR (DMSO-d6, 400 MHz) δ ppm 6.67 (m, 1H) 6.30 (m, 1H) 5.05 (bs, 2H) 3.38 (s, 3H) 1.93 (s, 3H).