反应详情

温度

20 °C

6-Bromo-3-methanesulfonyl-2-methyl-quinolin-4-ol (example C.1) (6 g, 19 mmol) and N,N-dimethyl-p-toluidine (5.5 mL, 38 mmol) were dissolved in toluene (60 mL) and heated under argon to reflux. The phosphorous oxychloride (1.9 mL, 20.9 mL) was added and heating at reflux continued for 6.5 h. The product precipitated spontaneously upon cooling to 20° C., the crystals were filtered off and washed with little toluene. One obtained 4.19 g (66%) of light brown crystals. Since the product is somewhat soluble in toluene, the mother liquor was extracted with 3 N HCl (2×), sat. NaCl (2×). The residue was purified by chromatography on silica gel in dichloromethane. One obtained 1.17 g (18%) of additional material. MS: m/z=333/335 (M).

1. temperatureheated under argon
2. temperatureto reflux
3. temperatureheating
4. temperatureat reflux
5. customThe product precipitated spontaneously
6. filtrationthe crystals were filtered off
7. washwashed with little toluene
8. customOne obtained 4.19 g (66%) of light brown crystals
9. extractionthe mother liquor was extracted with 3 N HCl (2×), sat. NaCl (2×)
10. customThe residue was purified by chromatography on silica gel in dichloromethane