HCID 67517858, compound → Ethyl 6-amino-1-benzofuran-3-carboxylate

HRID 2173348Notes

Reaction equation

HRID 2173348 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[C:12]1[CH:25]=[CH:24][C:15]2[C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][O:18][C:14]=2[CH:13]=1>CCO.O>[NH2:3][C:12]1[CH:25]=[CH:24][C:15]2[C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][O:18][C:14]=2[CH:13]=1

Participants

4

Reactant 1

HCID 67517858HCID 67517858, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl 6-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-benzofuran-3-carboxylate (4.7 g, 14.0 mmol) in 200 mL of EtOH was added NH2NH2H2O (6.3 mL, 107.1 mmol, 85% in water) dropwise and the mixture was stired for 2 h at room temperature. The solvent was removed under vacuum and the residue was dissolved in water. The mixture was extracted with EtOAc, and 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 ethyl 6-amino-1-benzofuran-3-carboxylate.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue was dissolved in water
  3. extractionThe mixture was extracted with EtOAc
  4. washthe combined organic phase was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified with silca gel column chromatograph

Sources & evidence

ORD record
ord-0b3e7cde4f1a444f9f4f7fbeb942a042
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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