Hydrochloric Acid → HCID 46935551, compound

HRID 1626727Notes

Reaction equation

HRID 1626727 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([NH:14][C:15](=[O:28])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[CH:27]=[CH:26][O:25][CH:24]=3)[CH:18]=2)=[C:8]([CH:13]=1)[C:9]([O:11]C)=[O:10].Cl>C1COCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([NH:14][C:15](=[O:28])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[CH:27]=[CH:26][O:25][CH:24]=3)[CH:18]=2)=[C:8]([CH:13]=1)[C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66680269HCID 66680269, compound

Product 1

HCID 46935551HCID 46935551, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

3 mL of THF and 1.2 mL of 1N aqueous sodium hydroxide were added to 0.30 g (0.81 mmol) of methyl 5-chloro-2-({[3-(furan-3-yl)phenyl]acetyl}amino)benzoate at room temperature, and the mixture was stirred at 50° C. for 2.5 hours. After cooling, 1N hydrochloric acid was added to acidify the reaction mixture. Thereafter, the solvent was distilled off under reduced pressure, and water was then added to the residue. Solids were collected by filtration, followed by drying, thereby giving 252 mg of the target 5-chloro-2-({[3-(furan-3-yl)phenyl]acetyl}amino)benzoic acid (yield: 88%).

Workup

  1. temperatureAfter cooling
  2. distillationThereafter, the solvent was distilled off under reduced pressure, and water
  3. additionwas then added to the residue
  4. filtrationSolids were collected by filtration
  5. customby drying

Sources & evidence

ORD record
ord-4ab3e942e0d742aba0f5649605087249
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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