Hydrogen Peroxide → 3-Carboxymethylsulfinyl-7-fluoro-1-methyl-4-quinolone

HRID 982873Notes

Reaction equation

HRID 982873 reaction equation
[OH:1]O.[C:3]([CH2:6][S:7][C:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([F:19])=[CH:14][CH:15]=2)[N:10]([CH3:20])[CH:9]=1)([OH:5])=[O:4]>C(O)(=O)C.O>[C:3]([CH2:6][S:7]([C:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([F:19])=[CH:14][CH:15]=2)[N:10]([CH3:20])[CH:9]=1)=[O:1])([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 11161467HCID 11161467, compound

Product 1

HCID 101254203-Carboxymethylsulfinyl-7-fluoro-1-methyl-4-quinolone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

50% hydrogen peroxide (57 ml, 33.6 mg, 0.988 mmol) was added to a solution of 3-carboxymethylthio-7-fluoro-1-methyl-4-quinolone (4) in acetic acid (3.6 ml) at 60° C. and the mixture was stirred at 55° C. for 4 h. The hot mixture was diluted with water (12 ml) and cooled to 0° C. A white solid that precipitated was filtered off and dried under high vacuum. The yield of 3-Carboxymethylsulfinyl-7-fluoro-1-methyl-4-quinolone was 185 mg (72.7%) (5).

Workup

  1. temperaturecooled to 0° C
  2. customA white solid that precipitated
  3. filtrationwas filtered off
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-e0af859a191949b68f2a8ebcf088cd70
Source dataset
uspto-grants-2005_03
Patent number
US06861528B2

Reaction notes

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