4-Chloro-6-(Methylsulfonyl)quinoline synthesis

8synthesis methods

Product Name:4-Chloro-6-(Methylsulfonyl)quinoline
CAS Number:454705-62-5
Molecular formula:C10H8ClNO2S
Molecular Weight:241.69

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Yield:454705-62-5 92%

Reaction Conditions:

with trichlorophosphate at 110; for 2 h;

Steps:

6.3

6-(Methylsulfonyl)-4-quinolinol (23 g, 103 mmol) and phosphorus oxychloride (380 mL, 4.1 mol) were combined and heated at 110° C. for 2 h. The reaction was concentrated to dryness. The residue was treated with satd. sodium carbonate (CAUTION: gas evolution) to quench any residual POCl₃. The suspension was diluted with water and filtered to provide pure 4-chloro-6-(methylsulfonyl)quinoline (23 g, 95 mmol, 92% yield). ¹H NMR (500 MHz, DMSO-d₆) δ 9.05 (d, J=4.9 Hz, 1H), 8.74 (s, 1H), 8.29-8.40 (m, 2H), 7.98 (d, J=4.6 Hz, 1H), 3.39 (s, 3H); MS (m/z) 242 (M+H⁺).

References:

US2012/41024,2012,A1 Location in patent:Page/Page column 17-18

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References

1,3-Dioxane-4,6-dione, 2,2-dimethyl-5-[[[4-(methylsulfonyl)phenyl]amino]methylene]-

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References

ethyl 4-hydroxy-6-(methylthio)quinoline-3-carboxylate

26893-09-4
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References

4-hydroxy-6-(methylthio)-3-quinolinecarboxylic acid

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References