Ammonium Chloride → 1-(5-Amino-1-benzofuran-2-yl)ethanone

HRID 729269Notes

Reaction equation

HRID 729269 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12](=[O:14])[CH3:13])=[CH:9][C:8]=2[CH:15]=1)([O-])=O.[NH4+].[Cl-]>CCO.O.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12](=[O:14])[CH3:13])=[CH:9][C:8]=2[CH:15]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 5200231-(5-Nitro-1-benzofuran-2-YL)ethanone

Product 1

HCID 37833671-(5-Amino-1-benzofuran-2-yl)ethanoneYield 54.3%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Iron powder (0.680 g, 12.19 mmol) was added in portions to a solution of 1-(5-nitro-1-benzofuran-2-yl)ethanone (0.500 g, 2.44 mmol) and NH4Cl (0.652 g, 12.19 mmol) in EtOH (15 mL) and water (4 mL) and the mixture was refluxed for 1 h. The mixture was filtered through Celite and washed out with DCM. The solvents were evaporated and the residue was dissolved in DCM. The organic layer was washed with water, dried through a phase separator and evaporated. The product was purified by silica gel column chromatography using a EtOAc/hexane/MeOH (49:49:2) as eluant, to give the title compound (0.232 g, 54%) as a yellow solid; 1H NMR (500 MHz, CD3OD): δ 7.50 (ds, 1H), 7.33 (d, 1H), 6.95-7.00 (m, 2H), 2.54 (s, 3H); Mass Spectrum: M+H+ 176.

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. filtrationThe mixture was filtered through Celite
  3. washwashed out with DCM
  4. customThe solvents were evaporated
  5. dissolutionthe residue was dissolved in DCM
  6. washThe organic layer was washed with water
  7. customdried through a phase separator
  8. customevaporated
  9. customThe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6e2ca894c03e4085a87d43753bd61737
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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