Ethyl 4-(5-amino-3-methyl-4-oxo-1,4-dihydroquinolin-8-yl)cyclohex-3-ene-1-carboxylate → HCID 178472343, compound

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Reaction Steps

A mixture of ethyl 4-(5-amino-3-methyl-4-oxo-1,4-dihydroquinolin-8-yl)cyclohex-3-ene-1-carboxylate (Compound 304C, 0.270 g, 0.83 mmol) and palladium 10% wt on activated carbon (88.0 mg, 0.083 mmol) in EtOH (2.17 mL) was evacuated and purged with hydrogen (3×) and subsequently stirred under one atmosphere of hydrogen at rt for 16 hrs. The reaction mixture was filtered and the filtrate was concentrated in vacuo to an orange oil. The product was purified by mass directed purification which resolved the cis and trans isomers. Compound 304A, the trans isomer eluted first: 1H NMR (400 MHz, MeOD) δ ppm 1.27 (t, J=7.07 Hz, 3 H) 1.53-1.73 (m, 4 H) 1.79 (d, J=4.29 Hz, 2 H) 2.02 (d, J=0.76 Hz, 3 H) 2.26 (d, J=13.14 Hz, 2 H) 2.70-2.82 (m, 2 H) 4.17 (q, J=7.07 Hz, 2 H) 6.38 (d, J=8.34 Hz, 1 H) 7.12 (d, J=8.34 Hz, 1 H) 7.63 (s, 1 H). MS (ES+): m/z 329.16/329.36 (100/70) [MH+]. HPLC: tR=1.28 min (Micromass TOF: polar—3 min). Compound 304B, the cis isomer eluted after: 1H NMR (400 MHz, CDCl3) δ ppm 1.25 (t, J=7.07 Hz, 3 H) 1.54 (br. s., 1 H) 1.70 (d, J=12.63 Hz, 1 H) 1.87 (br. s., 1 H) 2.02 (d, J=0.51 Hz, 1 H) 2.07 (br. s., 1 H) 2.35-2.45 (m, 1 H) 2.69-2.81 (m, 1 H) 4.12 (q, J=7.07 Hz, 1 H) 6.39 (d, J=8.34 Hz, 1 H) 7.20 (d, J=8.34 Hz, 1 H) 7.64 (d, J=0.76 Hz, 1 H). MS (ES+): m/z 329.14/329.35 (100/70) [MH+]. HPLC: tR=1.30 min (Micromass TOF: polar—3 min).

Provenance & Evidence