Hydrochloric Acid → HCID 58306888, compound

HRID 1909860Notes

Reaction equation

HRID 1909860 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:3]=1[CH:4]=[C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:7](=[O:14])[O:6]1.[OH-].[Na+].Cl>C(O)C>[Cl:19][C:16]1[CH:15]=[C:3]2[C:2](=[CH:18][CH:17]=1)[NH:1][C:5]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:7]([OH:6])=[O:14])=[CH:4]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66868258HCID 66868258, compound

Product 1

HCID 58306888HCID 58306888, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(2-amino-5-chlorobenzylidene)-2-benzofuran-1(3H)-one (466 mg) in ethanol (3.5 mL) was added a 1 M aqueous sodium hydroxide solution (3.4 mL) at room temperature, followed by heating with reflux for 45 minutes. The reaction mixture was acidified by adding of 1 M hydrochloric acid under ice-cooling, and stirred at room temperature for 1 hour. The resulting precipitate was separated by filtration and the filtrate was extracted with diethyl ether. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 2-(5-chloro-1H-indol-2-yl)benzoic acid (395 mg).

Workup

  1. temperatureby heating
  2. temperaturewith reflux for 45 minutes
  3. temperaturecooling
  4. customThe resulting precipitate was separated by filtration
  5. extractionthe filtrate was extracted with diethyl ether
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ae9e4c7651dd45e18e6fe91820f8684f
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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