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With hydrogen In tetrahydrofuran; methanol at 60℃; for 22 h;
Step A: rac-7-Methoxy-indan-1-ylamine A mixture of 7-methoxy-indan-1-one oxime (CAS 908108-58-7, (E)-oxime 179899-16-2) (22.3 g, 126 mmol)) and Raney-Nickel (11.26 g) in tetrahydrofuran (570 mL) and methanol (570 mL) was hydrogenated at 100 bar hydrogen-pressure at 60° C. for 22 h. Filtered the catalyst off, washed with methanol and tetrahydrofuran, all volatiles were removed in vacuum to give the title compound as a brown oil (19.95 g, 97percent, HPLC 0.4 min), MS (ISP) m/e=164.2 [(M+H)+].
64%
With hydrogen In ethanol at 23℃; for 16 h;
Step A: rac-7-Methoxy-indan-1-ylamine A mixture of 7-methoxy-indan-1-one oxime (CAS no: 908108-58-7, (E)-oxime 179899-16-2) (4.59 g, 25.9 mmol) in ethanol (500 mL) with 10percent palladium on carbon (4.59 g) was hydrogenated at 23° C. and atmospheric pressure for 16 h. Filtered the catalyst off, washed with ethanol, evaporated the filtrate totally and dried in high vacuum to give the title compound as a brown oil (2.7 g, 64percent); MS: m/e=164.2 (M+H+).
41%
With hydrogen In methanol for 120 h;
Step B 7-Methoxy-indan-1-one oxime (5 g, 28 mmol) was suspended in 250 mL methanol. Palladium on charcoal (10percent, 0.3 g) was added and the reaction was hydrogenated with a hydrogen ballon for 5 days. Palladium on charcoal was filtered off and the filtrate was evaporated. The title compound was obtained as a yellow liquid (1.89, 41percent) and used without any further purification for the next step.
With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 140℃; for 2h;
Step B: rac-(7-Methoxy-indan-1-yl)-(6-nitro-quinolin-2-yl)-amine A mixture of <strong>[29969-57-1]2-chloro-6-nitro-quinoline</strong> (1.8 g, 8.62 mmol) in 1-methyl-2-pyrrolidone (5 mL) with the above described 7-methoxy-indan-1-ylamine (1.69 g, 10.35 mmol) and N-ethyldiisopropylamine (2.22 mL, 12.94 mmol) was stirred at 140 C. for 2 h. Cooled to 23 C., poured onto water and extracted twice with ethyl acetate, dried over Na2SO4 and evaporated totally to give a crude product which was purified by silica gel column chromatography with heptane/dichloromethane followed by trituration with diethyl ether to give the title compound as a yellow solid (2.3 g, 80%); MS: m/e=336.3 (M+H+).
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