反应详情

温度

90 °C

A mixture of 2-(4-methoxyphenyl)acetamide (1.51 g, 9.14 mmol) and N,N-dimethylformamide dimethyl acetal (6 ml, 45.0 mmol) in a r.b.f, equipped with a Dean-Stark trap was placed in a 120° C. bath (turned to solution once heated) for 1.5 hours. The reaction was cooled and concentrated, then, added AcOH (18 ml), hydrazine hydrate (0.611 ml, 10.06 mmol), and heated at 90° C. for 1.5 hours. After cooling to RT, added 2M aqueous sodium hydroxide and extracted 3 times with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with MeOH in DCM to afford the title compound. Mass spectrum (ESI) 190.3 (M+1).

1. customequipped with a Dean-Stark trap
2. customwas placed in a 120° C.
3. temperatureonce heated) for 1.5 hours
4. temperatureThe reaction was cooled
5. concentrationconcentrated
6. temperatureAfter cooling to RT
7. extractionextracted 3 times with ethyl acetate
8. washThe combined organics were washed with brine
9. dry with materialdried over sodium sulfate
10. filtrationfiltered
11. customthe solvent was evaporated under reduced pressure
12. customThe residue was purified by flash column chromatography on silica gel
13. washeluting with MeOH in DCM