Reaction #607444

Reaction equation

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

ammonium chloride

→

title compound

Yield 100.5%

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

Yield 100.5%

Solvents

EtOH H2O

Conditions

Workup

1. 1
   Temperatureunder heating
2. 2
   Temperatureto reflux for 3 h
3. 3
   Otherwas consumed
4. 4
   Otherto reach room temperature
5. 5
   Filtrationwas filtered through a pad of celite
6. 6
   ConcentrationThe filtrate was concentrated under reduced pressure
7. 7
   Otherthe residue partitioned between a 2 molar aqueous NaOH solution (20 mL) and ethyl acetate (30 mL)
8. 8
   OtherThe phases were separated
9. 9
   Extractionthe aqueous phase extracted with ethyl acetate (2×20 mL)
10. 10
    WashThe organic layer was washed with brine (40 mL)
11. 11
    Dryingdried over anhydrous Na2SO4
12. 12
    Filtrationfiltered
13. 13
    OtherThe solvent was removed in vacuo

Procedure

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.

Source