Reacción #607444

Ecuación de reacción

3-bromo-2-(trans-4-isopropylcyclohexoxy)-6-methyl-5-nitro-pyridine

ammonium chloride

→

title compound

Rendimiento 100.5%

5-bromo-6-(trans-4-isopropylcyclohexoxy)-2-methyl-pyridin-3-amine

Rendimiento 100.5%

Disolventes

EtOH H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaunder heating
2. 2
   Temperaturato reflux for 3 h
3. 3
   Otrowas consumed
4. 4
   Otroto reach room temperature
5. 5
   Filtraciónwas filtered through a pad of celite
6. 6
   ConcentraciónThe filtrate was concentrated under reduced pressure
7. 7
   Otrothe residue partitioned between a 2 molar aqueous NaOH solution (20 mL) and ethyl acetate (30 mL)
8. 8
   OtroThe phases were separated
9. 9
   Extracciónthe aqueous phase extracted with ethyl acetate (2×20 mL)
10. 10
    LavadoThe organic layer was washed with brine (40 mL)
11. 11
    Secadodried over anhydrous Na2SO4
12. 12
    Filtraciónfiltered
13. 13
    OtroThe solvent was removed in vacuo

Procedimiento

To a stirred solution of 3-bromo-2-(trans-4-isopropylcyclohexoxy)-6-methyl-5-nitro-pyridine (0.917 g, 2.00 mmol) in EtOH/H2O (24 mL/6 mL, 4/1 v/v), ammonium chloride (0.109 g, 2.00 mmol, 1.0 eq) and iron powder (0.452 g, 8.00 mmol, 4 eq) were added at room temperature under inert atmosphere (Ar). The reaction mixture was stirred under heating to reflux for 3 h. At this point in time, TLC indicated that the starting material was consumed. Therefore, the reaction mixture was allowed to reach room temperature and was filtered through a pad of celite. The filtrate was concentrated under reduced pressure and the residue partitioned between a 2 molar aqueous NaOH solution (20 mL) and ethyl acetate (30 mL). The phases were separated and the aqueous phase extracted with ethyl acetate (2×20 mL). The organic layer was washed with brine (40 mL), dried over anhydrous Na2SO4 and filtered. The solvent was removed in vacuo to afford the title compound (0.658 g, 100%) as an oil.

Fuente