HCID 15735723, compound → 2-[[2-Chloro-3-(1-hydroxyethyl)phenyl]amino]benzoic acid

HRID 2051238Notes

Reaction equation

HRID 2051238 reaction equation
C1C=CC([I+][C:8]2[C:13]([C:14]([O-:16])=[O:15])=[CH:12][CH:11]=[CH:10][CH:9]=2)=CC=1.O.[NH2:18][C:19]1[C:20]([Cl:28])=[C:21]([CH:25]([CH3:27])[OH:26])[CH:22]=[CH:23][CH:24]=1>C(O)(C)C>[Cl:28][C:20]1[C:21]([CH:25]([OH:26])[CH3:27])=[CH:22][CH:23]=[CH:24][C:19]=1[NH:18][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=1[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 15735723HCID 15735723, compoundHCID 22271963(2-Carboxyphenyl)phenyliodonium hydrate (1:1)

Product 1

HCID 157357242-[[2-Chloro-3-(1-hydroxyethyl)phenyl]amino]benzoic acidYield 65.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of diphenyliodonium-2-carboxylate monohydrate (11.4 g, 33.3 mmol), 3-amino-2-chloro-α-methylbenzenemethanol (5.2 g, 30.3 mmol), and cupric acetate (0.5 g) in isopropanol (100 mL) is heated at reflux for 12 hours under an argon atmosphere. The solvent is evaporated under vacuum and the remaining dark oil is taken up in 10% aqueous KOH. The insoluble material is removed by filtration through Celite-545, and the filtrate is extracted with ether to remove nonacidic impurities. The aqueous solution is acidified to pH=3 with concentrated HCl. The resulting precipitate is collected by filtration and purified by column chromatography (silica, ethyl acetate) to give pure 2-[[2-chloro-3-(1-hydroxyethyl)phenylamino]benzoic acid (5.8 g, 60%), mp=169-171° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 12 hours under an argon atmosphere
  3. customThe solvent is evaporated under vacuum
  4. customThe insoluble material is removed by filtration through Celite-545
  5. extractionthe filtrate is extracted with ether
  6. customto remove nonacidic impurities
  7. filtrationThe resulting precipitate is collected by filtration
  8. custompurified by column chromatography (silica, ethyl acetate)

Sources & evidence

ORD record
ord-028b15ebcf4b4d1581ee51324ff8a9f9
Source dataset
uspto-grants-1991_05
Patent number
US05017604

Reaction notes

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