Formic Acid → 2-Hydroxy-5-[[4-[(5-methyl-3-isoxazolyl)aminosulfonyl]phenyl]ethynyl]benzoic acid

HRID 743024Notes

Reaction equation

HRID 743024 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([NH:24][C:25]3[CH:29]=[C:28]([CH3:30])[O:27][N:26]=3)(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].[OH-].[K+].C(O)C.C(O)=O>O>[OH:1][C:2]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([NH:24][C:25]3[CH:29]=[C:28]([CH3:30])[O:27][N:26]=3)(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:9][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 19423380Ethyl 2-hydroxy-5-[[4-[(5-methyl-3-isoxazolyl)aminosulfonyl]phenyl]ethynyl]benzoate

Product 1

HCID 194233722-Hydroxy-5-[[4-[(5-methyl-3-isoxazolyl)aminosulfonyl]phenyl]ethynyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-hydroxy-5-[[4-[(5-methyl-3-isoxazolyl)aminosulfonyl]-phenyl]ethynyl]benzoate (1.5 g) was added to a boiling solution of potassium hydroxide (6 g, 92 mmol) in water (100 ml). After 5 min, ethanol (25 ml) was added and the solution acidified with formic acid. The precipitate was collected by filtration, washed with water and dried. Yield 1.4 g, quantitative.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-f6fdc54510684d9ba9d759b4542b750d
Source dataset
uspto-grants-1996_09
Patent number
US05556855

Reaction notes

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