Ethyl 6-amino-1-benzofuran-3-carboxylate → HCID 67516008, compound

HRID 2173349Notes

Reaction equation

HRID 2173349 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:5]2[C:6]([C:9]([O:11][CH2:12]C)=[O:10])=[CH:7][O:8][C:4]=2[CH:3]=1>CO>[NH2:1][C:2]1[CH:15]=[CH:14][C:5]2[CH:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:7][O:8][C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 67515639Ethyl 6-amino-1-benzofuran-3-carboxylate

Product 1

HCID 67516008HCID 67516008, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 6-amino-1-benzofuran-3-carboxylate (2.0 g, 9.8 mmol) in 50 mL of MeOH was added Mg filings (1.17 g, 49 mmol) ans the mixtrue was stired overnight at room temperature. The mixture was filtered and the filtrate was concentrated. The residue was then partitioned between EtOAc and water. The combined organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified with silca gel column chromatograph to give methyl 6-amino-2,3-dihydro-1-benzofuran-3-carboxylate.

Workup

  1. additionwas added Mg filings (1.17 g, 49 mmol)
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was then partitioned between EtOAc and water
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified with silca gel column chromatograph

Sources & evidence

ORD record
ord-a2b4ea049567489aa6735e0434ab510c
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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