7-methoxy-2-(3-nitrobenzylidene)-3,4-dihydro-2H-napthalen-1-one → 3-aminobenzyl-7-methoxy-3,4-dihydro-2H-napthalen-1-one

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Reaction Steps

A mixture of 626 mg (2.02 mmol) of the product of Example 28 and 125 mg of 10% Pd/C in 15 mL tetrahydrofuran and 15 mL CH3OH was hydrogensted on a Parr (trademark) Hydrogenator under 25 psi H2 at room temperature. After 30 minutes, the reaction mixture was filtered through diatomaceous earth [Celite (trademark)], the filtrate concentrated in vacuo, and the residue purified by silica gel chromatography (5% ethyl acetate-CH2Cl2) to yield 369 mg of pure product, a yellow solid. m.p.: 159°-161° C. MS (LSIMS): 282 M+H, 155 Base; 1H NMR (AC 300, CDCl3): δ3.84 (s, 3H); 3.64 (br s, 2H, NH2); IR (cm31 1): 3360, 6450, 1665. Analysis calculated: C 76.85, H 6.81, N 4.98%; found: C 75.94, H 6.66, N 4.77%.

Provenance & Evidence