* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
General procedure: 4.3.1 4'-Methyl-4-aminobiphenyl (4a) Compound 3a (2.54 mmol, 541 mg) was dissolved in an EtOH/EtOAc 1:1 mixture (50 mL) and reduced by hydrogenation catalysed by Raney Nickel in an H-Cube at 65 °C at a flow rate of 0.8 mL/min, using full hydrogen mode. The solution obtained was concentrated under reduced pressure to give 480 mg of a yellow solid, which was purified by chromatography on silica gel, hexane/CH2Cl2 1:1, to give 440 mg of the pure expected product as an off-white solid (95percent yield).
Reference:
[1] Journal of the American Chemical Society, 2013, vol. 135, # 23, p. 8436 - 8439
[2] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 3057 - 3061
3
[ 106-38-7 ]
[ 170850-45-0 ]
Reference:
[1] Journal of the American Chemical Society, 2018,
4
[ 5350-93-6 ]
[ 5720-05-8 ]
[ 170850-45-0 ]
Reference:
[1] New Journal of Chemistry, 2017, vol. 41, # 24, p. 15420 - 15432
General procedure: 4.3.1 4'-Methyl-4-aminobiphenyl (4a) Compound 3a (2.54 mmol, 541 mg) was dissolved in an EtOH/EtOAc 1:1 mixture (50 mL) and reduced by hydrogenation catalysed by Raney Nickel in an H-Cube at 65 C at a flow rate of 0.8 mL/min, using full hydrogen mode. The solution obtained was concentrated under reduced pressure to give 480 mg of a yellow solid, which was purified by chromatography on silica gel, hexane/CH2Cl2 1:1, to give 440 mg of the pure expected product as an off-white solid (95% yield).
With polystyrene supported morpholine; In dichloromethane; at 20℃; for 16h;
General procedure: 4.4.1 N-(4'-Methylbiphenyl-4-yl)acetamide 6b. Compound 4a (0.33 mmol, 60 mg), 5b (0.70 mmol, 1.104 g mL-1, 50 muL), PS-NMM (0.70 mmol, 175 mg) and CH2Cl2 (10 mL) were stirred at rt for 48 h. The mixture was filtered and the filtrate was concentrated under reduced pressure. The crude product was purified by chromatography on silica gel, CH2Cl2/EtOAc 9:1, to give 77 mg of the pure expected product as an off-white solid (99% yield).
With iron; ammonium chloride; In ethanol; water; at 70 - 80℃; for 1h;
General procedure: Ethanol (20 ml) and water (5 ml) was mixed, added with iron powder, and heated to 70-80C. Ammonium chloride (0.1 g, 2.1 mmol) was added, followed by 2-phenyl-5-nitropyridine (2.0 g, 10.0 mmol) obtained in (i). The reaction was carried out at 70-80C for 1 hour. After the completion of the reaction, the iron powder was filtered while hot through Celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in isopropyl alcohol, crystallized and filtered with addition of water to give the title compound (1.4 g, 81.9%).
With iron; ammonium chloride; In ethanol; water; at 70 - 80℃; for 1h;
General procedure: Ethanol (20 ml) and water (5 ml) was mixed, added with iron powder, and heated to 70-80C. Ammonium chloride (0.1 g, 2.1 mmol) was added, followed by 2-phenyl-5-nitropyridine (2.0 g, 10.0 mmol) obtained in (i). The reaction was carried out at 70-80C for 1 hour. After the completion of the reaction, the iron powder was filtered while hot through Celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in isopropyl alcohol, crystallized and filtered with addition of water to give the title compound (1.4 g, 81.9%).
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water;Inert atmosphere; Reflux;
General procedure: To 0.329 g (1.5 mmol) 4-iodoaniline, 1.8 mmol ArB(OH)2, 0.318 g (3 mmol) Na2CO3 and 75 mg (0.075 mmol) PdCl2(PPh3)2, 15 mL of a blended solution of dioxane and water (v/v = 3/1) was added under N2 atmosphere. Then the reaction was heated to reflux and monitored by TLC. Upon cooling, the reaction mixture was dilute with sat. NH4Cl solution, then extracted with EA (3×20 mL), and the organic layer was washed with saturated NaCl aqueous solution, dried over anhydrous Na2SO4 and purified by flash chromatography to afford different 4-aminobiphenyl derivatives. According to the reductive amination procedure, the 4-aminobiphenyl derivative was further treated with salicylaldehyde and to afford the corresponding compound 5&6.
2-(((6-(p-tolyl)pyridin-3-yl)amino)methyl)phenol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
General procedure: Under an atmosphere of N2, 0.175 g (1 mmol) compd. 2 was dissolved in methanol, 0.11 mL (1.05 mmol) salicylaldehyde was added and stirred overnight at room temperature. When compd. 2 disappeared, NaBH4 (61 mg, 1.6 mmol) was added. After stirring for 10 min, the reaction was quenched by sat. NH4Cl solution, then extracted with CH2Cl2 (3×20 mL), and the organic layer was washed with saturated NaCl aqueous solution, dried over anhydrous Na2SO4 and purified by flash chromatography (PE:EtOAc = 15:1) to afford 0.230 g (82%) E6 as white solid.