Water → Flosequinoxan

HRID 1085912Notes

Reaction equation

HRID 1085912 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:12](=[O:18])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])=[C:6]([CH:11]=1)[N:7]([CH3:10])[CH:8]=O.O.[OH-].[Na+]>C(O)(C)C>[F:1][C:2]1[CH:11]=[C:6]2[C:5]([C:12](=[O:18])[C:13]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:8][N:7]2[CH3:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 867447425'-fluoro-N-methyl-2'-methylsulphonylacetylformanilide

Product 1

HCID 131270Flosequinoxan

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 5'-fluoro-N-methyl-2'-methylsulphonylacetylformanilide (5.0 g), prepared in a similar manner to that described in Example 11, water (50 ml) and isopropyl alcohol (50 ml) was heated to 50°. Aqueous sodium hydroxide solution (1 M; 3 ml) was added and the mixture heated under reflux for 2.5 hours. The mixture was cooled in an ice bath and the product isolated by filtration, washed with water (10 ml), and then isopropyl alcohol (10 ml) to give the crude product (3.3 g). A sample of the crude product (2.0 g) was crystallised from industrial methylated spirit (112 ml) to give 7-fluoro-1-methyl-3-methylsulphonyl-4-quinolone, m.p 221.5°-223° (1.7 g). The product was heated at 90° with grinding to give 7-fluoro-1-methyl-3-methylsulphonyl-4-quinolone, m.p. 235°-236° (1.7 g).

Workup

  1. customprepared in a similar manner to that
  2. temperaturewas heated to 50°
  3. temperaturethe mixture heated
  4. temperatureunder reflux for 2.5 hours
  5. temperatureThe mixture was cooled in an ice bath
  6. customthe product isolated by filtration
  7. washwashed with water (10 ml)
  8. customisopropyl alcohol (10 ml) to give the crude product (3.3 g)
  9. customA sample of the crude product (2.0 g) was crystallised from industrial methylated spirit (112 ml)

Sources & evidence

ORD record
ord-64181bde2bb34e6d896e7d8c11f88a58
Source dataset
uspto-grants-1991_04
Patent number
US05011931

Reaction notes

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