반응 #80793

반응 방정식

hydrogen

hydrogen

2-Methoxycarbonyl-3-methylquinoline

→

cis-2-methoxycarbonyl-3-methyltetrahydroquinoline

수율 78.2%

용매

acetic acid

반응 조건

후처리

1. 1
   기타was consumed
2. 2
   농축concentrated in vacuo
3. 3
   기타The residue was purified by silica gel column chromatography with 20:1 to 10:1 hexane/ethyl acetate

실험 절차

2-Methoxycarbonyl-3-methylquinoline (30 g, 0.149 mol) in acetic acid (300 mL) was hydrogenated over platinum oxide (1 g) under atmospheric pressure of hydrogen at room temperature until the theoretical amount of hydrogen was consumed. The mixture was passed through celite and concentrated in vacuo. The residue was purified by silica gel column chromatography with 20:1 to 10:1 hexane/ethyl acetate to give 23.93 g of cis-2-methoxycarbonyl-3-methyltetrahydroquinoline (78%): 1H NMR (270 MHz, CDCl3) d 6.99 (m, 2H), 6.64 (t, 1H, J=7.9 Hz), 6.58 (d, 1H, J=7.9 Hz), 4.34 (s, 1H), 4.09 (t, 1H, J=2.5 Hz), 3.06 (dd, 1H, J =16.9, 5.8 Hz), 2.55 (m, 1H), 2.50 (dd, 1H, J=16.9, 3.3 Hz), 0.88 (d, 3H, J=6.9 Hz).

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