4-Chloro-6-methyl-2-nitro-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid → 2-Amino-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda *6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid

Participants

Reaction Steps

To a solution of the methyl ester of Example 32j (0.280 g, 0.7 mmols) in DMF (10 mL) was added activated Raney-Nickel (100 mg) and the reaction mixture was subjected to reduction in a Parr hydrogenator (20 psi, 2 h). The reaction mixture was filtered (celite bed), and the filtrate was poured onto crushed ice to obtain a solid which was subjected to hydrolysis as described in the synthesis of Example 1i to obtain the title compound. Yield: 76%; 1H NMR (DMSO-d6): δ 2.60 (s, 3H, CH3), 5.10 (s, 2H, CH2), 5.40 (s, 2H, NH2), 6.80 (d, 2H, Ar), 8.10 (s, 1H, Ar), 8.20 (s, 1H, Ar); MS: m/e (EI+) 354 (M+1).

Provenance & Evidence