反应详情

A mixture of 2-(3-chloropropoxy)-1-methoxy-4-nitrobenzene (2.15 g, 8.77 mmol) and tin (II) chloride dihydrate (6.1 g, 27.11 mmol) in 50 mL of ethyl acetate was heated at reflux for 6.5 hours. The reaction mixture was cooled to room temperature and poured into 250 mL of saturated aqueous sodium bicarbonate. After stirring for 40 minutes, additional ethyl acetate was added and the layers were separated. The organic layer was washed with saturated sodium bicarbonate and water then dried over magnesium sulfate and filtered. The solution was concentrated in vacuo and purified by flash column chromatography, eluting with 1:1 hexane: ethyl acetate, to provide 753 mg of 3-(3-chloropropoxy)-4-methoxyaniline as a dark brown oil; 1H NMR (400 MHz, DMSO-d6) δ 2.13 (m, 2H), 3.62 (s, 3H), 3.78 (t, J=6 Hz, 2H), 3.96 (t, J=6 Hz, 2H), 4.77 (br s, 2H), 6.10 (dd, J=8, 2 Hz, 1H), 6.29 (d, J=2 Hz, 1H), 6.66 (d, J=8 Hz, 1H); MS (ES) m/z216.1, 218.1 (M+H)+.

1. temperaturewas heated
2. temperatureat reflux for 6.5 hours
3. customthe layers were separated
4. washThe organic layer was washed with saturated sodium bicarbonate and water
5. dry with materialthen dried over magnesium sulfate
6. filtrationfiltered
7. concentrationThe solution was concentrated in vacuo
8. custompurified by flash column chromatography
9. washeluting with 1:1 hexane