Hydrochloric Acid → 2-Hydroxy-5-[[4-[(2-pyridinylamino)sulfonyl]phenyl]ethynyl]benzoic acid

HRID 1653891Notes

Reaction equation

HRID 1653891 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].Cl>[OH-].[Na+]>[OH:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:15]=[CH:16][C:17]([S:20]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)(=[O:22])=[O:21])=[CH:18][CH:19]=2)=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19423375Methyl 2-hydroxy-5-[[4-[(2-pyridinylamino)sulfonyl]phenyl]ethynyl]benzoate

Product 1

HCID 194234282-Hydroxy-5-[[4-[(2-pyridinylamino)sulfonyl]phenyl]ethynyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The ester from Example 1d (23.7 g, 58 mmol) was dissolved in 1M NaOH (190 ml) and refluxed for 6 h. The cooled solution was acidified with an excess of 6M HCl. The precipitated formed was allowed to stand for 2 h, filtered off and washed with water (3×200 ml). The white product was dried at 60° C. in vacuo. Yield 21.7 g (95%).

Workup

  1. temperaturerefluxed for 6 h
  2. customThe precipitated formed
  3. filtrationfiltered off
  4. washwashed with water (3×200 ml)
  5. customThe white product was dried at 60° C. in vacuo

Sources & evidence

ORD record
ord-72aa83ece39840ccb8607696e8b3764f
Source dataset
uspto-grants-1995_04
Patent number
US05403930

Reaction notes

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