1,3-dimethyl-7-nitroquinolin-4(1H)-one → 5-amino-1,3-dimethylquinolin-4(1H)-one

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A mixture of 1,3-dimethyl-5-nitroquinolin-4(1H)-one and 1,3-dimethyl-7-nitroquinolin-4(1H)-one Compound 299B, 2.2 g, 10 mmol) in MeOH (150 mL) was hydrogenated over 5% Pd/C (0.8 g) at 40° C. under 40 psi hydrogen pressure overnight. The catalyst was filtered off and the filtrate was concentrated and purified by HPLC to give the title compound (540 mg, 28%) as a pure regioisomer. 1H NMR (DMSO-d6, 400 MHz): δ=1.92 (s, 3 H), 3.69 (s, 3 H), 6.63 (d, J=8.0 Hz, 1 H), 6.80 (d, J=8.4 Hz, 1 H), 7.40 (t, J=8.0 Hz, 1 H), 7.91 (s, 1 H).

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