Sodium Hydroxide → 3-(Aminosulfonyl)-4-fluorobenzoic acid

HRID 17848Notes

Reaction equation

HRID 17848 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].FC1C=CC(C)=CC=1N.[OH-:22].[Na+].[Mn]([O-])(=O)(=O)=[O:25].[K+]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:25])=[O:22])=[CH:4][C:3]=1[S:9](=[O:11])(=[O:10])[NH2:12]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 2629702-Fluoro-5-methylanilineHCID 516875Potassium PermanganateHCID 35471672-Fluoro-5-methylbenzenesulfonamide

Product 1

HCID 6848423-(Aminosulfonyl)-4-fluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 2-fluoro-5-methylbenzenesulphonamide (5.3 mmol), obtained according to the process described in Step A of Example 1 starting from 2-fluoro-5-methylaniline, in water (50 mL) is heated at 70° C. and then NaOH 10% w/v is added dropwise until the compound has completely dissolved. Potassium permanganate (3 g) is added in small portions. After stirring for 4 hours, the suspension is discharged by filtration in the hot state and the filtrate is brought to pH 1 by adding 12N HCl. The precipitate obtained is collected by filtration, washed with water and dried to yield the title product in the form of a white solid.

Workup

  1. customobtained
  2. dissolutionhas completely dissolved
  3. filtrationthe suspension is discharged by filtration in the hot state
  4. additionby adding 12N HCl
  5. customThe precipitate obtained
  6. filtrationis collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-096df4f75def4fc0af51d27068220afa
Source dataset
uspto-grants-2010_06
Patent number
US07741320B2

Reaction notes

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