反应详情

温度

600 °C

A mixture of 2-(2-chloro-ethoxy)-6-nitro-phenylamine (1a, 3.0 g, 13.8 mmol) and benzylamine (9.0 g, 84.0 mmol) was heated neat at 100-1100° C. for 6 hr. The excess benzylamine was removed by distillation under vacuum (70-75° C./0.1 mm). The residue was poured into 1 N sodium hydroxide (300 mL) and extracted with ethyl acetate (2×, 300 mL). The combined organic layer was washed with water (2×, 300 mL) and brine (300 mL). The ethyl acetate layer was dried over anhydrous magnesium sulfate, filtered, and the solvent removed under vacuum to give 5.1 g of crude red oil. Purification by chromatography (500 g silica gel, ethyl acetate: 2 M NH3 in methanol, 20:1) afforded 3.54 g (89.3%) of a red semi-solid, mp 33-60° C.; MS EI m/e 287 (M+).

1. customThe excess benzylamine was removed by distillation under vacuum (70-75° C./0.1 mm)
2. additionThe residue was poured into 1 N sodium hydroxide (300 mL)
3. extractionextracted with ethyl acetate (2×, 300 mL)
4. washThe combined organic layer was washed with water (2×, 300 mL) and brine (300 mL)
5. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
6. filtrationfiltered
7. customthe solvent removed under vacuum
8. customto give 5.1 g of crude red oil
9. customPurification by chromatography (500 g silica gel, ethyl acetate: 2 M NH3 in methanol, 20:1)