2-(4-tert-Butoxycarbonyl-2-nitro-benzylidene)-succinic Acid Dimethyl Ester → 3-Methoxycarbonylmethyl-2-oxo-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid tert-butyl ester

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Reaction Steps

A solution of 2-(4-tert-butoxycarbonyl-2-nitro-benzylidene)-succinic acid dimethyl ester (5.0 g, 13.2 mmol) in methanol (40 mL) with 10% Pd/C was hydrogenated at 50 psi and 25° C. for 20 h. The reaction mixture was filtered to afford after evaporation in vacuo the title compound as a gray solid (3.56 g, 85%). NMR (dmso-d6, 200 MHz) : δ1.5 (s, 9H, tert-butyl), 2.7-3.4 (m, 5H, CH2CHCH2), 3.6 (s, 3H, CH3), 7.2-7.5 (m, 3H, ArH), 10.3 (s, 1H, NH).

Provenance & Evidence