反应详情

温度

15 °C

5-Chloro-2-methyl-4-nitroaniline (1.0 g, 5.3 mmol, 1.0 equiv) was dissolved in AcOH (46 mL) and cooled to 15° C. NaNO2 (0.37 g, 5.3 mmol, 1.0 equiv) was dissolved In H2O (1 mL) and added all at once via pipet. The reaction was warmed to room temperature and stirred for 28 hours. The reaction mixture was concentrated en vacuo to provide an orange solid, which was azeotroped several times with hexanes. The solid was dissolved in EtOH (12 mL) and added to a solution of SnCl2 (3.4 g, 18 mmol, 3.4 equiv) in 6N HCl (12 mL) The reaction mixture was heated to 60° C. for two hours, then cooled to room temperature and basified with 50% NaOH. The resulting precipitate was removed by filtration and washed with EtOAc. The filtrate was transferred to a separatory funnel and the phases were separated. The aqueous phase was extracted with EtOAc, and the combined organic phases were dried over Na2SO4. The solution was filtered, and the filtrate was concentrated in vacuo. The resulting residue was purified by flash chromatography (25% EtOAc/CH2Cl2) to afford 170 mg (19%) of the title compound as a pale yellow solid.

1. additionadded all at once via pipet
2. temperatureThe reaction was warmed to room temperature
3. concentrationThe reaction mixture was concentrated en vacuo
4. customto provide an orange solid, which
5. customwas azeotroped several times with hexanes
6. dissolutionThe solid was dissolved in EtOH (12 mL)
7. temperaturewas heated to 60° C. for two hours
8. customThe resulting precipitate was removed by filtration
9. washwashed with EtOAc
10. customThe filtrate was transferred to a separatory funnel
11. customthe phases were separated
12. extractionThe aqueous phase was extracted with EtOAc
13. dry with materialthe combined organic phases were dried over Na2SO4
14. filtrationThe solution was filtered
15. concentrationthe filtrate was concentrated in vacuo
16. customThe resulting residue was purified by flash chromatography (25% EtOAc/CH2Cl2)