تفاعل #607442

معادلة التفاعل

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

ammonium chloride

→

title compound

المردود 101.5%

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

المردود 101.5%

المذيبات

EtOH H2O

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةunder heating to reflux
2. 2
   أخرىwas consumed at this point in time
3. 3
   ترشيحfiltered through a pad of celite
4. 4
   تركيزThe resulting filtrate was concentrated in vacuo
5. 5
   أخرىthe residue partitioned between a 2 molar aqueous NaOH solution (100 mL) and ethyl acetate (150 mL)
6. 6
   أخرىAfter phase separation
7. 7
   استخلاصthe aqueous phase was extracted once more with ethyl acetate (2×100 mL)
8. 8
   غسيلThe organic layer was washed with brine (400 mL)
9. 9
   تجفيفdried over anhydrous Na2SO4
10. 10
    ترشيحfiltered
11. 11
    أخرىThe solvent was removed in vacuo

الإجراء التجريبي

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.

المصدر