Reaction #159822

Reaction equation

2-Fluoroaniline

methyl 2-phenylsulfonyl-3-ethoxy-acrylate

→

4-hydroxy-3-phenylsulfonyl-8-fluoroquinoline

Yield 3.3%

Solvents

biphenyl ether

Conditions

Workup

1. 1
   workup.DISTILLATIONEthanol was distilled during the first 30 min
2. 2
   Temperaturewas cooled
3. 3
   Filtrationthe formed solid was filtered off
4. 4
   workup.DISSOLUTIONdissolved in ethanol
5. 5
   FiltrationAfter filtration from charcoal ethanol
6. 6
   Otherwas evaporated
7. 7
   OtherThe residue after evaporation of fractions
8. 8
   Washwas washed with ether, it

Procedure

2-Fluoroaniline 7(1) (3.82 g, 0.0344 mol) and methyl 2-phenylsulfonyl-3-ethoxy-acrylate 7(2) (9.59 g, 0.0355 mol) were mixed together in biphenyl ether (21.5 ml). The mixture was stirred in an opened flask for 6 h at 250-270° C. Ethanol was distilled during the first 30 min. After the reaction was completed (LCMS control) the mixture was cooled, the formed solid was filtered off, dissolved in ethanol and solution was boiled with charcoal. After filtration from charcoal ethanol was evaporated, the residue was subjected to chromatography on silica, eluent—gradient of solvent system CHCl3:ethyl acetate=from 10:1 to 5:1. The residue after evaporation of fractions, comprising the final product was washed with ether, it gave 345 mg (3.3%) of 4-hydroxy-3-phenylsulfonyl-8-fluoroquinoline 7(3).

Source