ChemicalBook CAS DataBase List 7-Nitro-1-tetralone

7-Nitro-1-tetralone synthesis

8synthesis methods

Product Name:7-Nitro-1-tetralone
CAS Number:40353-34-2
Molecular formula:C10H9NO3
Molecular Weight:191.18

529-34-0 Synthesis

529-34-0
482 suppliers
$6.00/10g

40353-34-2
126 suppliers
$8.00/250mg

51114-73-9 Synthesis

51114-73-9
87 suppliers
$13.00/250mg

Yield:51114-73-9 16% ，40353-34-2 77%

Reaction Conditions:

with sulfuric acid;nitric acid at 0; for 1 h;

Steps:

125
Λ/-(5,6,7,8-Tetrahydro-2-naphthalenyl)acetamide (166). fHNO₃ (8.6 mL, 144 mmol) in CH₂SO₄ (50 mL) was added dropwise to a stirred solution of α-tetralone (165) (20 g, 137 mmol) in CH₂SO₄ (300 mL) at 0 ⁰C and the solution stirred for 1 h. The solution was poured into ice/water (2 L), stirred for 30 min, filtered and washed with water. The solid was dried and purified by chromatography, eluting with 20% EtOAc/pet. ether, to give (i) 5-nitro-3,4-dihydro-1(2H)-naphthalenone (4.1 g, 16%) as a white solid: ¹H NMR δ 8.35 (dd, J = 7.8, 1.4 Hz, 1 H, H-6), 8.09 (dd, J = 8.0, 1.4 Hz, 1 H, H-8), 7.48 (br t, J = 7.9 Hz, 1 H, H-7), 3.22 (t, J = 6.1 Hz, 2 H, H-4), 2.74 (dd, J = 6.8, 6.4 Hz, 2 H, H-2), 2.13-2.21 (m, 2 H, H-3); and (ii) 7-nitro-3,4-dihydro-1(2H)-naphthalenone (20.1 g, 77%) as a white solid: ¹H NMR δ 8.86 (d, J = 2.5 Hz, 1 H, H-4), 8.30 (dd, J = 8.4, 2.5 Hz, 1 H, H-6), 7.46 (d, J = 8.4 Hz, 1 H, H-5), 3.09 (t, J = 6.1 Hz, 2 H, H-4), 2.74 (dd, J = 7.0, 6.2 Hz, 2 H, H-2), 2.17- 2.25 (m, 2 H, H-3).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 cHCI (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 x 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 Ac₂O (1.8 mL, 19.2 mmol) was added dropwise to the solution at 0 ⁰C. The solution was stirred at 20 ⁰C 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 Λ/-(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, 2 H, H-1, NH), 7.15 (dd, J = 8.2, 2.1 Hz, 1 H, H-3), 7.00 (d, J = 8.2 Hz, 1 H, H-4), 2.69-2.77 (m, 4 H, 2 x CH₂), 2.15 (s, 3 H, CH₃), 1.74-1.80 (m, 4 H, 2 x 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).