反应详情

To 3-methoxy-4-methylaniline (1.0 g, 7.29 mmol) in refluxing in 6N HCl (50 mL) was added dropwise (E)-but-2-enal (1.02 g, 14.6 mmol). The reaction was heated to reflux for 2 hours then cooled down and neutralized with NH4OH. The organic phase was extracted with DCM and the combined organic phases dried over MgSO4, filtered and concentrated under reduced pressure to leave a dark residue. The residue was purified by reverse phase chromatography (SP4, 25M, eluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes) to yield 7-methoxy-2,6-dimethylquinoline (580 mg, 29.7% yield) as a beige solid.

1. temperatureThe reaction was heated
2. temperatureto reflux for 2 hours
3. temperaturethen cooled down
4. extractionThe organic phase was extracted with DCM
5. dry with materialthe combined organic phases dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customto leave a dark residue
9. customThe residue was purified by reverse phase chromatography (SP4, 25M
10. washeluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes)