Sodium Hydroxide → HCID 86595225, compound

Participants

Reaction Steps

Stir a mixture of 1-amino-7-nitro-1,2,3,4-tetrahydronaphthalen-2-ol (500 mg, 2.40 mmol) and 1N NaOH (4.8 mL, 4.8 mmol) in a mixture of 50 mL of toluene and 50 mL of water for 30 minutes. Added biphenyl-4-carbonyl chloride (570 mg, 2.64 mmol) slowly and stir for four hours at room temperature. Remove the solid by filtration, and wash with toluene. Evaporate solvent under reduced pressure. Biphenyl-4-carboxylic acid (2-hydroxy-7-nitro-1,2,3,4-tetrahydro-naphthalen-1-yl)-amide is obtained in 54% as a white solid: 1H NMR (DMSO-d6) δ 8.87 (1H, d, J=8.4 Hz), 8.03 (2H, d, J=8.4 Hz), 7.99 (2H, d, J=7.6 Hz), 7.79 (2H, d, J=8.4 Hz), 7.74 (2H, d, J=8.4 Hz), 7.50 (2H, t, J=7.2 Hz), 7.43(2H, t, J=6.8 Hz), 5.22 (1H, d, J=4.4 Hz), 5.11 (1H, t, J=7.6 Hz), 3.95-4.01 (1H, m), 2.87-3,07(2H, m), 2.08-2.15 (1H, m), 1.81-1.94 (1H, m); MS 389(MH+). The above compound (0.25 g, 0.64 mmol) is reduced in 10 mL of DMF with 48 mg of 10% Pd-C at room temperature under 60 psi (414 kPa) for overnight to form biphenyl-4-carboxylic acid (7-amino-2-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-amide, obtained in 96% as a yellow oil. MS 359 (MH+).

Provenance & Evidence