HCID 22262102, compound → HCID 45089717, compound

Participants

Reaction Steps

Methyl 3-nitro-5,6,7,8-tetrahydronaphthalene-1-carboxylate (see Zh Obshch Khim; 1948, 877-884; 1.4 g, 3 mmol), which was contaminated with its regioisomer methyl 4-nitro-5,6,7,8-tetrahydronaphthalene-1-carboxylate (1:1), was dissolved in methanol (50 mL). The solution was flushed with nitrogen whereupon Pd/C (5%) catalyst (0.19 g) was added. The mixture was stirred under H2 at room temperature until the consumption of gas ceased. The catalyst was removed by filtration and then the solvent was evaporated. The product was separated from its 4-amino regioisomer and by-products by chromatography on silica gel using CH2Cl2 and triethylamine (98:2). There was obtained 0.24 g (39%) of methyl 3-amino-5,6,7,8-tetrahydronaphthalene-1-carboxylate as an oil. 1H NMR (500 MHz, CDCl3): 1.7-1.8 (m, 4H), 2.7 (m, 2H), 2.9 (m, 2H), 3.8 (s, 3H), 6.6 (d, 1H), 7.0 (d, 1H).

Provenance & Evidence