Methyl 5-nitrobenzofuran-2-carboxylate → Methyl 5-aminobenzofuran-2-carboxylate

HRID 1455847Notes

Reaction equation

HRID 1455847 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:8]=2[CH:9]=1)=[O:4].[H][H]>C1COCC1.[Pd]>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:8]=2[CH:9]=1)=[O:4]

Participants

5

Reactant 2

HCID 12148807Methyl 5-nitrobenzofuran-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 10845388Methyl 5-aminobenzofuran-2-carboxylateYield 98.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The product from step (a) (6.9 g) was dissolved in THF (200 mL), followed by the addition of 10% Pd/C (1 g), and the resulting reaction mixture was hydrogenated under 50 psi of hydrogen for 2 hours. The catalyst was removed by filtration through celite, and the solvent was removed in vacuo to provide 5.9 g of the title compound.

Workup

  1. customthe resulting reaction mixture
  2. customThe catalyst was removed by filtration through celite
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5a9a99d015964f03bf53bbf35fac070c
Source dataset
uspto-grants-2009_01
Patent number
US07482368B2

Reaction notes

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