반응 #607442

반응 방정식

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

ammonium chloride

→

title compound

수율 101.5%

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

수율 101.5%

용매

EtOH H2O

반응 조건

후처리

1. 1
   온도under heating to reflux
2. 2
   기타was consumed at this point in time
3. 3
   여과filtered through a pad of celite
4. 4
   농축The resulting filtrate was concentrated in vacuo
5. 5
   기타the residue partitioned between a 2 molar aqueous NaOH solution (100 mL) and ethyl acetate (150 mL)
6. 6
   기타After phase separation
7. 7
   추출the aqueous phase was extracted once more with ethyl acetate (2×100 mL)
8. 8
   세척The organic layer was washed with brine (400 mL)
9. 9
   건조dried over anhydrous Na2SO4
10. 10
    여과filtered
11. 11
    기타The solvent was removed in vacuo

실험 절차

To a stirred solution of 3-bromo-2-(cis-4-isopropylcyclohexoxy)-6-methyl-5-nitro-pyridine (22.59 g, 63.24 mmol) in EtOH/H2O (600 mL/150 mL, 4/1 v/v), ammonium chloride (3.45 g, 63.24 mmol, 1.0 eq) and iron powder (14.27 g, 253.0 mmol, 4 eq) were added at room temperature under inert atmosphere (Ar). The reaction mixture was stirred for 3 h under heating to reflux. As TLC indicated that the starting material was consumed at this point in time, the reaction mixture was cooled to room temperature and filtered through a pad of celite. The resulting filtrate was concentrated in vacuo and the residue partitioned between a 2 molar aqueous NaOH solution (100 mL) and ethyl acetate (150 mL). After phase separation, the aqueous phase was extracted once more with ethyl acetate (2×100 mL). The organic layer was washed with brine (400 mL), dried over anhydrous Na2SO4 and filtered. The solvent was removed in vacuo to afford the title compound (21.01 g, 101%) in the form of an oil.

출처