7-Nitro-1-tetralone → N-(5,6,7,8-Tetrahydronaphthalen-2-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

A solution of 7-nitro-3,4-dihydro-1(2H)-naphthalenone (1.67 g, 8.7 mmol) in EtOAc/EtOH (1:1, 150 mL), water (15 mL) and cHCl (2 mL) with Pd/C (5%, 500 mg) was stirred vigorously under H2 (60 psi) for 16 h. The suspension was filtered through Celite, washed with EtOH (4×10 mL) and the organic solvent evaporated. The aqueous residue was partitioned between DCM and dilute aqueous NH3 solution and the organic fraction dried and the solvent evaporated. The residue was dissolved in dioxane (20 mL), and AcO (1.8 mL, 19.2 mmol) was added dropwise to the solution at 0° C. The solution was stirred at 20° C. for 16 h, diluted with water (50 mL), and partitioned between EtOAc and dilute aqueous NH3 solution. The organic fraction was washed with water (3×20 mL), dried and the solvent evaporated to give N-(5,6,7,8-tetrahydro-2-naphthalenyl)acetamide 166 (1.57 g, 95%) as a white solid: 1H NMR δ 7.18-7.25 (m, 2H, H-1, NH), 7.15 (dd, J=8.2, 2.1 Hz, 1H, H-3), 7.00 (d, J=8.2 Hz, 1H, H-4), 2.69-2.77 (m, 4H, 2×CH2), 2.15 (s, 3H, CH3), 1.74-1.80 (m, 4H, 2×CH2). The procedure was repeated a number of times to give N-(5,6,7,8-tetrahydro-2-naphthalenyl)acetamide 166 (10.21 g, 88% overall).

Provenance & Evidence