Sodium Bicarbonate → Methyl 2-(4-aminophenyl)benzofuran-7-carboxylate

HRID 1761909Notes

Reaction equation

HRID 1761909 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=[CH:15][C:13]=3[CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=[CH:15][C:13]=3[CH:14]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 14229713Methyl 2-(4-nitrophenyl)benzofuran-7-carboxylate

Product 1

HCID 14229714Methyl 2-(4-aminophenyl)benzofuran-7-carboxylateYield 93.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3.1 g of methyl 2-(4-nitrophenyl)benzofuran-7-carboxylate, 11.7 g of stannous chloride dihydrate and 100 ml of ethyl acetate is heated at 70° C. for 1 hour. After cooling, the reaction mixture is alkalized with an aqueous sodium bicarbonate solution and extracted with ethyl acetate. The extract is washed with water, dried and evaporated to remove solvent to give 2.6 g of methyl 2-(4-aminophenyl)benzofuran-7-carboxylate as yellow crystals.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. customevaporated
  6. customto remove solvent

Sources & evidence

ORD record
ord-a5c7623183c14b62b81be3b37ab22eab
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Reaction notes

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