反应详情

A suspension of iron (3.81 g, 70 mmol) and ammonium chloride (5.47 g, 102 mmol) in 80 mL of ethanol and 25 mL of water was heated to reflux. 1-Ethoxy-2-iodo-4-nitrobenzene (5.0 g, 20 mmol) was added in portions and the reaction was heated at reflux for 1 hour. The hot mixture was filtered through Celite, washed with hot ethanol. The filtrate was concentrated in vacuo and treated with ethyl acetate and water. The organic layer was extracted, washed with brine, dried over magnesium sulfate and filtered. Removal of the solvent in vacuo provided 5.1 g of (4-ethoxy-3-iodophenyl)amine as a light brown oil; 1H NMR (400 MHz, DMSO-d6) δ 1.30 (s, 3H), 3.89 (q, 2H), 4.82 (bs, 2H), 6.53 (dd, 1H), 6.72 (d, 1H), 7.11 (d, 1H); MS (ES) m/z263.9 (M+H)+

1. temperaturewas heated to reflux
2. temperaturethe reaction was heated
3. temperatureat reflux for 1 hour
4. filtrationThe hot mixture was filtered through Celite
5. washwashed with hot ethanol
6. concentrationThe filtrate was concentrated in vacuo
7. additiontreated with ethyl acetate and water
8. extractionThe organic layer was extracted
9. washwashed with brine
10. dry with materialdried over magnesium sulfate
11. filtrationfiltered
12. customRemoval of the solvent in vacuo