Water → 2-AMINO-5-(AMINOSULFONYL)-4-FLUOROBENZOIC ACID

HRID 1106231Notes

Reaction equation

HRID 1106231 reaction equation
C([NH:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([S:12](=[O:15])(=[O:14])[NH2:13])=[CH:7][C:6]=1[CH3:16])(=O)C.[OH2:17].[OH2:18].O.O.O.O.O.S([O-])([O-])(=O)=O.[Mg+2].O.[Mn]([O-])(=O)(=O)=O.[K+]>[OH-].[Na+]>[F:11][C:9]1[CH:10]=[C:5]([NH2:4])[C:6](=[CH:7][C:8]=1[S:12](=[O:14])(=[O:15])[NH2:13])[C:16]([OH:18])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 24843Magnesium Sulfate HeptahydrateHCID 516875Potassium PermanganateHCID 20553706N-(5-Fluoro-2-methyl-4-sulfamoylphenyl)acetamide

Product 1

HCID 205536982-AMINO-5-(AMINOSULFONYL)-4-FLUOROBENZOIC ACID

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 25.0 g (0.102 molecule) of purified sulphonamide (4), 36.7 g of magnesium sulphate heptahydrate and of 560 ml of water was stirred and heated to 80°. Potassium permanganate (48.1 g) was added, in portions, keeping the temperature between 80° and 85°. The mixture was taken to 90° during 4 hours, filtered hot and the cake, (collected into a mass), of manganese dioxide was washed with water. The filtrate was acidified with concentrated hydrochloric acid and the precipitate of compound 5 was recovered. The moist compound 5 of the above reaction and 4.0 g., previously obtained, were heated under reflux for three hours in 215 ml of 3N sodium hydroxide. The reaction mixture was filtered and the filtrate was acidified with concentrated hydrochloric acid. The separating solid was recovered on a filter, washed with water, then dried in vacuo at 80°; yield: 20.1 g (70.5%).

Workup

  1. temperatureheated to 80°
  2. customthe temperature between 80° and 85°
  3. filtrationfiltered hot
  4. customthe cake, (collected into a mass), of manganese dioxide
  5. washwas washed with water
  6. customthe precipitate of compound 5 was recovered
  7. customThe moist compound 5 of the above reaction and 4.0 g
  8. custom, previously obtained
  9. temperaturewere heated
  10. filtrationThe reaction mixture was filtered
  11. customThe separating solid was recovered on a filter
  12. washwashed with water
  13. customdried in vacuo at 80°

Sources & evidence

ORD record
ord-40d09223609a4ebfbab21e2f4b1a2384
Source dataset
uspto-grants-1982_01
Patent number
US04312862

Reaction notes

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