Hydrochloric Acid → 5-Chloro-2-({[3-(furan-3-yl)phenyl]carbonyl}amino)benzoic acid

HRID 1626725Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:25]=[CH:24][O:23][CH:22]=3)[CH:16]=2)=[O:14])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:25]=[CH:24][O:23][CH:22]=3)[CH:16]=2)=[O:14])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

Conditions

Temperature: 50 °C

Procedure

0.61 g (1.7 mmol) of methyl 5-chloro-2-({[3-(furan-3-yl)phenyl]carbonyl}amino)benzoate was dissolved in 20 mL of THF solvent, and 4 mL of 1N aqueous sodium hydroxide was added. The mixture was stirred at 50° C. for 1.5 hours. After cooling, 1N hydrochloric acid was added to acidify the reaction mixture. Thereafter, the solvent was distilled off under reduced pressure. Subsequently, water was added to the residue, and solids were collected by filtration and washed with water. The obtained crude product was recrystallized using a mixed solvent of ethyl acetate and n-hexane, thereby giving 0.24 g of the target 5-chloro-2-({[3-(furan-3-yl)phenyl]carbonyl}amino)benzoic acid (yield: 41%).

Workup

temperatureAfter cooling
distillationThereafter, the solvent was distilled off under reduced pressure
additionSubsequently, water was added to the residue, and solids
filtrationwere collected by filtration
washwashed with water
customThe obtained crude product
customwas recrystallized

Sources & evidence

ORD record: ord-38c31f20f81e485ab7bbb80efb220d58
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785473B2

Reaction notes

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