6-Chloro-2-fluoro-3-(propane-1-sulfonamido)benzoic acid → 2-Fluoro-3-(propylsulfonamido)benzoic acid

HRID 1639587Notes

Reaction equation

HRID 1639587 reaction equation
Cl[C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([F:11])[C:5]([NH:12][S:13]([CH2:16][CH2:17][CH3:18])(=[O:15])=[O:14])=[CH:4][CH:3]=1>CO.[OH-].[OH-].[Pd+2]>[F:11][C:6]1[C:5]([NH:12][S:13]([CH2:16][CH2:17][CH3:18])(=[O:15])=[O:14])=[CH:4][CH:3]=[CH:2][C:7]=1[C:8]([OH:10])=[O:9]

Participants

4

Reactant 1

HCID 580875006-Chloro-2-fluoro-3-(propane-1-sulfonamido)benzoic acid

Product 1

HCID 580865772-Fluoro-3-(propylsulfonamido)benzoic acid

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To 6-chloro-2-fluoro-3-(propane-1-sulfonylamino)-benzoic acid (14, 0.69 g, 2.3 mmol) in 10 mL of methanol, 20% palladium hydroxide on carbon (200 mg) was added. The reaction was stirred under hydrogen at 50 psi for 2 hours. The reaction was filtered and the filtrate concentrated under vacuum to provide the desired compound 15 as a white solid that was used in the next step. MS(ESI) [M−H+]−=260.1. Additional material was prepared similarly for use in the next step.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-708817e2db2c484e94b1ac2de1e4f27c
Source dataset
uspto-grants-2012_02
Patent number
US08110576B2

Reaction notes

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