反应详情

Tin(II)chloride dihydrate (11.9 g, 52.6 mmol) was added to a solution of 2-methoxy-5-(1-methyl-cyclopropyl)-1,3-dinitro-benzene (2.21 g, 8.76 mmol) in ethyl acetate (30 mL). The mixture was heated to reflux for 0.25 h upon which the solution became red in color. The solution was cooled to rt and poured onto aqueous 2.0 M NaOH. The aqueous phase was extracted with ethyl acetate and the combined organic layers were washed with saturated NaHCO3. The organic layers were dried over sodium sulfate, eluted through a plug of silica gel (1% ammonium hydroxide in methylene chloride), and the filtrate was concentrated. The residue was redissolved in Et2O and extracted (3×) with 1.0 M HCl. The pH of the combined aqueous layers was adjusted to pH=12 with 2.0M NaOH and extracted with methylene chloride. The combined organic layers were dried over sodium sulfate, filtered and concentrated to provide 2-methoxy-5-(1-methyl-cyclopropyl)-benzene-1,3-diamine (860 mg, 52%) as a red oil. ESI MS (m/z 193, M+H).

1. temperatureThe mixture was heated
2. temperatureto reflux for 0.25 h upon which the solution
3. extractionThe aqueous phase was extracted with ethyl acetate
4. washthe combined organic layers were washed with saturated NaHCO3
5. dry with materialThe organic layers were dried over sodium sulfate
6. washeluted through a plug of silica gel (1% ammonium hydroxide in methylene chloride)
7. concentrationthe filtrate was concentrated
8. dissolutionThe residue was redissolved in Et2O
9. extractionextracted (3×) with 1.0 M HCl
10. extractionextracted with methylene chloride
11. dry with materialThe combined organic layers were dried over sodium sulfate
12. filtrationfiltered
13. concentrationconcentrated