Hydrochloric Acid → HCID 23698895, compound

HRID 1464166Notes

Reaction equation

HRID 1464166 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[C:30]([CH3:31])=[CH:29][CH:28]=[CH: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+:33].C(OCC)(=O)C.Cl>O>[OH:1][C:2]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:16]=[CH:17][C:18]([S:21]([NH:24][C:25]3[C:30]([CH3:31])=[CH:29][CH:28]=[CH:27][N:26]=3)(=[O:23])=[O:22])=[CH:19][CH:20]=2)=[CH:9][C:3]=1[C:4]([O-:6])=[O:5].[K+:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 19423387Ethyl 2-hydroxy-5-[[4-[(3-methyl-2-pyridinylamino)sulfonyl]phenyl]ethynyl]benzoate

Product 1

HCID 23698895HCID 23698895, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-hydroxy-5-[[4-[(3-methyl-2-pyridinylamino)sulfonyl]phenyl]ethynyl]benzoate (15.5g, 35 mmol) was refluxed in potassium hydroxide (10 g, 0.15 mol) in water (100 ml) for I h. After cooling to ca 70° C., ethyl acetate (50 ml) was added and hydrochloric acid was added to reach pH 7-8. Cooling with sniffing and then filtration gave directly 8.5 g of the product (51%).

Workup

  1. temperatureAfter cooling to ca 70° C.
  2. temperatureCooling
  3. filtrationfiltration

Sources & evidence

ORD record
ord-984c6f4b69d44ae6b134f3e06a305680
Source dataset
uspto-grants-1994_04
Patent number
US05302718

Reaction notes

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