Ammonium formate → 2-Phenylbenzofuran-7-carboxylic acid

HRID 1761905

Reaction equation

HRID 1761905 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:17]([OH:19])=[O:18])[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:7][C:6]=2[CH:16]=1.C([O-])=O.[NH4+]>CO.[C].[Pd]>[C:10]1([C:8]2[O:9][C:5]3[C:4]([C:17]([OH:19])=[O:18])=[CH:3][CH:2]=[CH:16][C:6]=3[CH:7]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 142297055-Chloro-2-phenylbenzofuran-7-carboxylic acid

Product 1

HCID 142297062-Phenylbenzofuran-7-carboxylic acid

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

1.46 g of 5-chloro-2-phenylbenzofuran-7-carboxylic acid are dissolved in a mixture of 15 ml of ethyleneglycol monomethylethers and 15 ml of methanol. 500 mg of 10% palladium-carbon and 1.6 g of ammonium formate are added to the solution and the solution is heated at 40° C. for 1.5 hours. The reaction mixture is filtered and the filtrate is concentrated under reduced pressure. The residue is dissolved in ethyl acetate. The solution is washed successively with 10% hydrochloric acid and water, dried and evaporated to remove solvent to give 2-phenylbenzofuran-7-carboxylic acid.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washThe solution is washed successively with 10% hydrochloric acid and water
  5. customdried
  6. customevaporated
  7. customto remove solvent

Sources & evidence

ORD record
ord-b34affb6ac8946c39bb7e90c5008713e
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Linked notes

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