Hydrochloric Acid → 2-(4-Dimethylaminophenyl)benzofuran-7-carboxylic acid

HRID 1761911Notes

Reaction equation

HRID 1761911 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=[CH:14][C:12]=3[CH:13]=2)=[CH:5][CH:4]=1.[OH-].[Na+].Cl>CO.O1CCCC1>[CH3:1][N:2]([CH3:22])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:10][C:11]3[C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=[CH:14][C:12]=3[CH:13]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14229715Methyl 2-(4-dimethylaminophenyl)benzofuran-7-carboxylate

Product 1

HCID 142297162-(4-Dimethylaminophenyl)benzofuran-7-carboxylic acidYield 99.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

920 mg of methyl 2-(4-dimethylaminophenyl)benzofuran-7-carboxylate are dissolved in a mixture of 20 ml of methanol and 20 ml of tetrahydrofuran. 10 ml of an aqueous 1N sodium hydroxide solution are added to the solution and the mixture is heated at 50° C. for 40 minutes. After cooling, the reaction mixture is neutralized with 10% hydrocloric acid and extracted with ethyl acetate. The extract is dried and evaporated to remove solvent to give 870 mg of 2-(4-dimethylaminophenyl)benzofuran-7-carboxylic acid as yellow powder.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. customThe extract is dried
  4. customevaporated
  5. customto remove solvent

Sources & evidence

ORD record
ord-89298c6253404621aebc81862be82b30
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Reaction notes

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