Reaction #674290

Reaction equation

3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine

Water

Na2CO3

→

3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine

Yield 96.0%

Solvents

EtOH AcOH

Conditions

Workup

1. 1
   TemperatureThe mixture was then refluxed for 75 min
2. 2
   FiltrationThe precipitate was collected by filtration
3. 3
   ConcentrationThe filtrate was concentrated by evaporator and in vacuo
4. 4
   Otherto give black residue
5. 5
   Extractionextracted with ether (3×200 mL)
6. 6
   WashThe combined ethereal solution was washed with saturated NaHCO3 (2×60 mL), H2O (60 mL) and brine (60 mL)
7. 7
   Dryingdried over anhydrous Na2SO4
8. 8
   Concentrationconcentrated by evaporator in vacuo

Procedure

To a suspension of 3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine (10 g, 30 mmol) in EtOH/AcOH (200/250 mL) was added iron powder (16.75 g, 300 mmol) in one portion. The mixture was then refluxed for 75 min. The reaction mixture was allowed to cool to room temperature. The precipitate was collected by filtration. The filtrate was concentrated by evaporator and in vacuo to give black residue. The black residue was combined with the collected solid. Water (300 mL) was added and the aqueous mixture was neutralized with Na2CO3, then extracted with ether (3×200 mL). The combined ethereal solution was washed with saturated NaHCO3 (2×60 mL), H2O (60 mL) and brine (60 mL), dried over anhydrous Na2SO4, concentrated by evaporator in vacuo to afford 3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine (8.67 g, 96%) as an off-white solid.

Source