HCID 59452704, compound → 2-(Ethyloxy)-4-(4-pyridinyl)aniline
Reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[CH3:2]>CCOC(C)=O.CO>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)[CH:7]=[CH:8][C:9]=1[NH2:10])[CH3:2]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
4-[3-(Ethyloxy)-4-nitrophenyl]pyridine (3.57 g, 14.62 mmol) was place in a 250 mL high pressure vessel and dissolved in 60 mL of 1 to 1 EtOAc/MeOH. 5 wt % Platinum(sulfided)/carbon (2.85 g, 0.73 mmol) was added followed quickly by a rubber septum. The flask was evacuated and filled with N2 six times to remove any oxygen. The vessel was then pressurized with H2 (60 psi). The solution stirred for 6 hours. The vessel was evacuated and filled with N2 six times to remove any H2. The solution was filtered through celite and evaporated to give the title compound of step C (2.62 g, 12.2 mmol, 83%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.44-8.48 (m, 2H), 7.57 (dd, J=4.58, 1.46 Hz, 2H), 7.16-7.21 (m, 2H), 6.70 (d, J=7.87 Hz, 1H), 5.09 (bs, 2H), 4.09 (q, J=6.96 Hz, 2H), 1.34 (t, J=6.96 Hz, 3H).