4-(Ethylamino)-3-nitrobenzonitrile → 3-Amino-4-(ethylamino)benzonitrile
Reaction equation
[CH2:1]([NH:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[N+:12]([O-])=O)[CH3:2]>[Pd].CCOC(C)=O>[NH2:12][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:4]=1[NH:3][CH2:1][CH3:2])[C:8]#[N:9]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A 250 mL pressure flask was sparged with a stream of nitrogen and then charged with 4-ethylamino-3-nitrobenzonitrile (1.6 g, 8.5 mmol), EtOAc (35 mL) and 10% w/w Pd/C (1.0 g, 11 mol %). The pressure flask was affixed to a Parr hydrogenation apparatus, evacuated briefly and backfilled with argon (2 cycles), then evacuated briefly and backfilled with hydrogen (3 cycles). The flask was pressurized to 50 psi of hydrogen and shaken vigorously. After 3 h, the flask was vented and sparged with a stream of nitrogen for 5 min. The reaction mixture was filtered through Celite and concentrated under reduced pressure to give the title product (1.4 g, quant.) as a pale brown solid. 1H-NMR (CDCl3): δ 7.14 (1H, dd), 6.91 (1H, d), 6.56 (1H, d), 3.91 (1H, br s), 3.32 (2H, br s), 3.19 (2H, q), 1.31 (3H, t).