Hydrochloric Acid → Flosequinoxan

HRID 1085913Notes

Reaction equation

HRID 1085913 reaction equation
[O-]CC.[Na+].[Na].[F:6][C:7]1[CH:8]=[CH:9][C:10]([C:17](=[O:23])[CH2:18][S:19]([CH3:22])(=[O:21])=[O:20])=[C:11]([CH:16]=1)[N:12]([CH3:15])[CH:13]=O.Cl>C(O)C>[F:6][C:7]1[CH:16]=[C:11]2[C:10]([C:17](=[O:23])[C:18]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:13][N:12]2[CH3:15])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 867447425'-fluoro-N-methyl-2'-methylsulphonylacetylformanilide

Product 1

HCID 131270Flosequinoxan

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A solution of sodium ethoxide in ethanol, prepared from sodium metal (2.3 g) and absolute ethanol (50 ml), was added dropwise over 5 minutes to a solution of 5'-fluoro-N-methyl-2'-methylsulphonylacetylformanilide (2.7 g), prepared in a similar manner to that described in Example 11, in absolute ethanol (10 ml) at ambient temperature. The mixture was stirred at this temperature for 30 minutes then added to hydrochloric acid (1M; 100 ml), keeping the temperature below 30°. The mixture was extracted with dichloromethane (2×150 ml). The extracts were combined, dried (magnesium sulphate) and evaporated in vacuo to give the crude product (2.5 g). The crude product was crystallised from industrial methylated spirit to give 7-fluoro-1-methyl-3-methylsulphonyl-4-quinolone, m.p. 221°-222.5° (2.0 g). The product was heated to 90° with grinding to give 7-fluoro-1-methyl-3-methylsulphonyl-4-quinolone, m.p. 234°-235° (2.0 g).

Workup

  1. customprepared in a similar manner to that
  2. customthe temperature below 30°
  3. extractionThe mixture was extracted with dichloromethane (2×150 ml)
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated in vacuo
  6. customto give the crude product (2.5 g)
  7. customThe crude product was crystallised from industrial methylated spirit

Sources & evidence

ORD record
ord-82b658e029b640a6b84356bf8923a24c
Source dataset
uspto-grants-1991_04
Patent number
US05011931

Reaction notes

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