반응 #309068

반응 방정식

3-(4-nitrophenoxy)pyridine

→

desired product

수율 95.4%

4-(pyridin-3-yloxy)aniline

수율 95.4%

용매

diethyl ether

EtOAc

반응 조건

후처리

1. 1
   기타purged with nitrogen (5×)
2. 2
   기타evacuated
3. 3
   기타The reaction mixture was then purged with nitrogen
4. 4
   여과filtered through a pad of Celite®
5. 5
   세척rinsing with ethyl acetate (3×) and ethanol (3×)
6. 6
   기타The filtrate was evaporated at reduced pressure
7. 7
   기타to give a brown crystalline residue
8. 8
   여과filtered

실험 절차

A solution of 3-(4-nitrophenoxy)pyridine (5.00 g, 23.13 mmol) in EtOAc (100 mL) in a 250 ml Parr bottle was purged with nitrogen. To this solution was added EtOAc-moistened 10% Pd/C catalyst (500 mg, 10% by weight). The reaction flask was placed in a Parr hygrogenation apparatus, purged with nitrogen (5×), evacuated, and then pressurized to 40 psi with hydrogen and shaken for 3.5 h. The reaction mixture was then purged with nitrogen, and filtered through a pad of Celite®, rinsing with ethyl acetate (3×) and ethanol (3×). The filtrate was evaporated at reduced pressure to give a brown crystalline residue. The residue was stirred in diethyl ether at room temperature for 16 h and then filtered to provide 4.11 g (95%) of the desired product as light brown crystals. 1H-NMR (DMSO-d6) δ 8.21 (m, 2H), 7.30 (ddd, J=8.4, 4.6, 0.7 Hz, 1H), 7.18 (ddd, J=8.4, 2.9, 1.4 Hz, 1H), 6.79 (d, J=8.8 Hz, 2H), 6.58 (d, J=9.0 Hz, 2H), 5.05 (br s, 2H); MS LC-MS [M+H]+=187, RT=1.03 min.

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