Ethanol → HCID 59457937, compound

Participants

Reaction Steps

To a refluxing suspension of amine E2 (5.46 g, 0.02 mol) in 2:1 EtOH:H2O (100 mL) were sequentially added Fe dust (4.97 g, 0.09 mol) and AcOH (2 mL, 2% v/v), and the resulting dark brown suspension was refluxed for ˜14 h. After this time, the hot reaction mixture was filtered through a pad of Celite, and solvent was removed under reduced pressure. The resulting residue was extracted with hot water, and the resulting aqueous suspension filtered through a pad of Celite. Solvent was removed under reduced pressure, and the residue extracted again with hot water. The resulting aqueous suspension was filtered through a pad of Celite. Solvent was removed to afford amine E3 as a brown-white crystalline solid (4.85 g, quantitative). 1H NMR [CD3)2SO]: 2.01 [s, 3H, ArCH3], 5.68 [s, 1H, ArNHAr], 5.88 [br s, 2H, ArNH2], 6.51 [ddd, J=9.67, 4.85, 2.94 Hz, 2H, ArH], 7.14 [d, J=8.52 Hz, 2H, ArH], 8.35 [s, 1H, ArH]. LCMS (APCI+): 216 (100%).

Provenance & Evidence