2,2-Diethyl-1,2,3,4-tetrahydro-7-nitroquinoline → 7-Amino-2,2-diethyl-1,2,3,4-tetrahydroquinoline

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Reaction Steps

This compound was prepared in a manner similar to that described for 7-amino-1,2,3,4-tetrahydro-2,2-dimethylquinoline (structure 19 of Scheme III, where R1=R2=Me) from for 2,2-diethyl-1,2,3,4-tetrahydro-7-nitroquinoline (0.311 g, 1.33 mmol) and 10% Pd/C (31 mg, 10% by weight) in EtOAc (4.0 mL) and EtOH (4.0 mL) to afford 255 mg (94%) of 7-amino-2,2-diethyl-1,2,3,4-tetrahydroquinoline. Data for 7-amino-2,2-diethyl-1,2,3,4-tetrahydroquinoline: Rf 0.26 (4:1 hexanes:ethyl acetate); 1H NMR (400 MHz, CDCl3) 6.77 (d, J=7.9H, 1H), 6.12 (dd, J=7.9,1.9,1H), 6.05 (d,J=2.0,1H), 4.68 (broad s,3H), 2.62 (t, J=6.7, 2H), 1.67 (t, J=6.7, 2H), 1.38-1.55 (m, 4H), 0.85 (t, J=7.4, 6H). P 2,2-Diethyl-7-fluoro-1,2,3,4-tetrahydro-6-trifluoromethyl-8-pyridono[5,6-g]quinoline (Compound 120, Structure 20 of Scheme III, where R1, R2=Et, R3=trifluoromethyl, R4=F)

Provenance & Evidence