반응 #614904

반응 방정식

2-{[4-methyl-3-(methyloxy)phenyl]oxy}-5-nitropyridine

water

ammonium chloride

→

title compound

수율 92.5%

6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinamine

수율 92.5%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   여과The catalyst was filtered off
2. 2
   workup.ADDITIONthe solution was diluted with an aqueous saturated solution of Na2CO3 (5 mL)
3. 3
   추출extracted with ethyl acetate (2 times 40 mL)
4. 4
   건조Combined organic layers were dried over sodium sulphate
5. 5
   여과filtered
6. 6
   기타evaporated
7. 7
   기타the residue was purified by silica gel chromatography (Biotage system with a 50 g SNAP column)
8. 8
   기타Evaporation

실험 절차

To a solution of 2-{[4-methyl-3-(methyloxy)phenyl]oxy}-5-nitropyridine (Reference Intermediate R3, 568 mg) in tetrahydrofuran (25 mL)/water (12.50 mL), iron (609 mg, 10.91 mmol) and then ammonium chloride (584 mg, 10.91 mmol) were added and the reaction mixture was stirred for 8 hours at room temperature. The catalyst was filtered off and the solution was diluted with an aqueous saturated solution of Na2CO3 (5 mL) and extracted with ethyl acetate (2 times 40 mL). Combined organic layers were dried over sodium sulphate, filtered and evaporated and the residue was purified by silica gel chromatography (Biotage system with a 50 g SNAP column) using a as eluent a gradient cyclohexane/ethyl acetate from 8/2 to 1/1. Evaporation afforded the title compound as light yellow oil (465 mg).

출처