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

HRID 742997Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12]=[CH: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-].[K+]>[OH:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12]=[CH: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

Conditions

Temperature: 100 °C

Procedure

Methyl 2-hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoate (12 g, 29 mmol) was dissolved in 1M KOH (120 ml) and the solution was refluxed for 7 h. The cooled solution was acidified with an excess of 1M hydrochloric acid. The precipitate was filtered off and washed with water (3×200 ml). The product was redissolved in a small portion of 1M NaOH. Water and dioxane (500+500 ml) was added and the solution was heated to 100° C. The solution was acidified with an excess of 1M HCl, and the product precipitated upon cooling. Yield 9 g (75%).

Workup

temperaturethe solution was refluxed for 7 h
filtrationThe precipitate was filtered off
washwashed with water (3×200 ml)
dissolutionThe product was redissolved in a small portion of 1M NaOH
additionWater and dioxane (500+500 ml) was added
customthe product precipitated
temperatureupon cooling

Sources & evidence

ORD record: ord-7b3829ac84b24df4af82d39f5b87942f
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05556855

Reaction notes

Loading…