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

HRID 2196636Notes

Reaction equation

HRID 2196636 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.[H][H]>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

5

Reactant 2

HCID 580875006-Chloro-2-fluoro-3-(propane-1-sulfonamido)benzoic acidHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

6-Chloro-2-fluoro-3-(propylsulfonamido)benzoic acid (0.5 g, 1.69 mmol) was dissolved in methanol (15 mL), and Pearlman's catalyst (one weight equivalent, 0.5 g, 20% Pd(OH)2 on carbon, 50% by weight water) was added. This mixture was subjected to a balloon of hydrogen for 3 hours and then filtered through GF/F filter paper. The filtrate was concentrated to 2-fluoro-3-(propylsulfonamido)benzoic acid (396 mg, 90%) as a solid. MS (M-H+) 262. NMR (DMSO-d6, 400 MHz) δ 13.36 (s, 1H), 9.76 (s, 1H), 7.58-7.70 (m, 2H), 7.26 (t, 1H, J=8), 3.10 (t, 2H, J=8), 1.69-1.80 (m, 2H), 0.98 (t, 3H, J=8).

Workup

  1. filtrationfiltered through GF/F
  2. filtrationfilter paper
  3. concentrationThe filtrate was concentrated to 2-fluoro-3-(propylsulfonamido)benzoic acid (396 mg, 90%) as a solid

Sources & evidence

ORD record
ord-478633d0c4fd4636a698fa55ab035a1f
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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