반응 #640619

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2-phenyl-4-hydroxy-7-methoxy-quinoline

phosphorus oxychloride

→

title compound

수율 91.0%

2-phenyl-4-chloro-7-methoxy-quinoline

수율 91.0%

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   온도under reflux
3. 3
   기타consumption of the starting material
4. 4
   workup.WAITThe reaction mixture was left
5. 5
   기타the solvent removed under vacuum
6. 6
   기타The residue was partitioned between ethyl acetate (100 mL) and 2M aqueous sodium hydroxide solution (80 mL)
7. 7
   기타the two layers were separated
8. 8
   세척The organic phase was washed with water (2×50 mL) and saturated aqueous sodium chloride solution (50 mL)
9. 9
   건조dried over sodium sulfate
10. 10
    여과filtered
11. 11
    기타the solvent removed under vacuum
12. 12
    기타The obtained beige solid was further dried under high vacuum for 2 hours

실험 절차

2-phenyl-4-hydroxy-7-methoxy-quinoline (2.73 g, 10.9 mmol., 1 eq) was suspended in neat phosphorus oxychloride (30 mL). The reaction mixture was heated under reflux. After 2 h, LCMS analysis showed full consumption of the starting material. The reaction mixture was left to cool to ambient temperature and the solvent removed under vacuum. The residue was partitioned between ethyl acetate (100 mL) and 2M aqueous sodium hydroxide solution (80 mL). The mixture was stirred at ambient temperature for a further 10 min, and then the two layers were separated. The organic phase was washed with water (2×50 mL) and saturated aqueous sodium chloride solution (50 mL), dried over sodium sulfate, filtered and the solvent removed under vacuum. The obtained beige solid was further dried under high vacuum for 2 hours to give 2.66 g (91%) of the title compound. 1H NMR (250 MHz, DMSO-d6) δ ppm 8.25-8.35 (m, 2H), 8.21 (s, 1 H), 8.09 (d, J=9.14 Hz, 1 H), 7.47-7.61 (m, 4H), 7.38 (dd, J=2.55, 9.18 Hz, 1 H), 3.97 (s, 3 H). LC-MS: purity 100% (UV), tR 2.58 min, m/z [M+1]+ 270.00.

출처