反应详情

SnCl2-dihydrate (1117 mg, 4.95 mmol) is added to a solution of N-Benzyl-N,2-dimethyl-5-nitro-aniline (247 mg, 0.96 mmol) in methanol (10 mL) and conc. HCl (1 mL). After boiling under reflux for 2.5 h, volatiles are evaporated under reduced pressure and the residue is partitioned between EtOAc and water, the pH being adjusted to approx. 10 by the addition of 2N NaOH. The organic layer is washed with sat. brine, dried (Na2SO4), and evaporated. Chromatography of the residue (silica gel, hexanes/EtOAc 3:2) yields N3-benzyl-N3,4-dimethyl-benzene-1,3-diamine.

1. temperatureunder reflux for 2.5 h
2. customvolatiles are evaporated under reduced pressure
3. customthe residue is partitioned between EtOAc and water
4. additionby the addition of 2N NaOH
5. washThe organic layer is washed with sat. brine
6. dry with materialdried (Na2SO4)
7. customevaporated