Reaktion #816451

Reaktionsgleichung

1-(5-nitro-1-benzofuran-2-yl)ethanone

NH4Cl

→

title compound

Ausbeute 54.3%

1-(5-Amino-1-benzofuran-2-yl)ethanone

Ausbeute 54.3%

Lösungsmittel

EtOH

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was refluxed for 1 h
2. 2
   FiltrationThe mixture was filtered through Celite
3. 3
   Waschenwashed out with DCM
4. 4
   SonstigeThe solvents were evaporated
5. 5
   workup.DISSOLUTIONthe residue was dissolved in DCM
6. 6
   WaschenThe organic layer was washed with water
7. 7
   Sonstigedried through a phase separator
8. 8
   Sonstigeevaporated
9. 9
   SonstigeThe product was purified by silica gel column chromatography

Vorschrift

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.

Quelle