2-Hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoic acid → 2-Hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]ethyl]benzoic acid

HRID 1653913Notes

Reaction equation

HRID 1653913 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[H][H]>O1CCCC1.C(O)(=O)C.[Pd]>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([S:19]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)(=[O:21])=[O:20])=[CH:17][CH:18]=2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 2

HCID 543430162-Hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 194234122-Hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]ethyl]benzoic acid

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoic acid (3 g, 7.5 mmol) in tetrahydrofuran (100 ml) and acetic acid (100 ml) was hydrogenated over palladium on charcoal (10%, 0.3g) and hydrogen at atmospheric pressure and room temperature for 27 h. The catalyst was filtered off and the solvent was evaporated. The residue was dissolved in a solution of sodium hydroxide (0.3 g) in acetone (30 ml) and water (30 ml). The solution was acidified with hydrochloric acid at ca 50° C. After cooling, the product crystallized yielding 1.6g (52%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in a solution of sodium hydroxide (0.3 g) in acetone (30 ml) and water (30 ml)
  4. customwas acidified with hydrochloric acid at ca 50° C
  5. temperatureAfter cooling
  6. customthe product crystallized
  7. customyielding 1.6g (52%)

Sources & evidence

ORD record
ord-43a0a8ccc3944eee8effda0d7b2c5b09
Source dataset
uspto-grants-1995_04
Patent number
US05403930

Reaction notes

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