4-Hydroxybenzylamine

Light Green Solid

Solid

4-Hydroxybenzylamine is an aromatic amine.

Preparation Example A+-1. Sodium 4-(((2-Aminopyridine-3-carbonyl)-amino)-methyl)-phenolate To a solution of 4-hydroxybenzaldehyde (10g, 81.9mmol) in methanol (45mL) was added Raney nickel (3g) and 7N aqueous ammonia solution (45mL), and the solution was stirred under hydrogen atmosphere (1 atm) at room temperature for 21 hours. The reaction solution was filtered through Celite pad to remove the catalyst, the filtrate was concentrated, and 4-aminomethyl-phenol (10g, quantitatively) was obtained as a pale green solid. Then, a solution of 2-aminonicotinic acid (3.0g, 21.7mmol) in N, N-dimethylformamide (30mL) was cooled with an ice water, 1-hydroxybenzotriazole (3.51 g, 26mmol), (3-dimethylaminopropyl)-ethyl-carbodiimide (4.04g, 26mmol) and a solution of the resulting 4-aminomethyl-phenol (3.0g, 21.7mmol) in N, N-dimethylformamide (20mL) were added, and the solution was stirred for 18 hours at this temperature. The reaction solution was partitioned into brine, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was dissolved in ethyl acetate, filtration was carried out using NH silica gel, and the filtrate was concentrated. The residue was dissolved in methanol (90mL), 1 N sodium hydroxide (17.8mL, 17.8mmol) was added thereto, followed by stirring at room temperature for an hour and a half. The reaction solution was concentrated in vacuo, and the title compound (5.66g) was obtained as a pale yellow solid.To a solution of 4-hydroxybenzaldehyde (10g, 81.9mmol) in methanol (45mL) was added Raney nickel (3g) and 7N aqueous ammonia solution (45mL), and the solution was stirred under hydrogen atmosphere (1 atm) at room temperature for 21 hours. The reaction solution was filtered through Celite pad to remove the catalyst, the filtrate was concentrated, and 4-aminomethyl-phenol (10g, quantitatively) was obtained as a pale green solid. Then, a solution of 2-aminonicotinic acid (3.0g, 21.7mmol) in N, N-dimethylformamide (30mL) was cooled with an ice water, 1-hydroxybenzotriazole (3.51g, 26mmol), (3-dimethylaminopropyl)-ethyl-carbodiimide (4.04g, 26mmol) and a solution of the resulting 4-aminomethyl-phenol (3.0g, 21.7mmol) in N, N-dimethylformamide (20mL) were added, and the solution was stirred for 18 hours at this temperature. The reaction solution was partitioned into brine, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was dissolved in ethyl acetate, filtration was carried out using NH silica gel, and the filtrate was concentrated. The residue was dissolved in methanol (90mL), 1 N sodium hydroxide (17.8mL, 17.8mmol) was added thereto, followed by stirring at room temperature for an hour and a half. The reaction solution was concentrated in vacuo, and the title compound (5.66g) was obtained as a pale yellow solid.Sodium hydroxide was added to dissolve 60kg 700kg of water, then add hydroxybenzaldehyde 150kg and stir until completely dissolved clear, the solution is sucked 2000L autoclave, and then put Raney nickel 25kg (wet weight), 25percent aqueous ammonia 500kg, added 8 hydrogen pressure, reaction temperature 50 up until hydrogen absorption had ceased, the cooling, pressure filtration of catalyst, washed with water and then 100kg.The catalyst was collected in buckets of water storage.The filtrate was transferred to a processing vessel, hydrochloric acid and then adjusting the pH value to 9 to 10, cooling to 5 Crystallization two hours, rejection filter, and dried to give p-hydroxy benzyl amine monohydrate 154kg, yield 88.9percent, HPLC purity 98.9percentMethanol (2.0L ) is charged in an autoclave, p-hydroxybenzaldehyde (250 gms; 2.049M) is added followed by 25 gms (50 gms wet) of Raney Nickel, and aqueous ammonia(25percent) ( 800ml ;11.7647M) . The hydrogenator is evacuated and flushed with nitrogen, a few times .The autoclave is initially pressurized to 3 Kg/cm with hydrogen and then maintained at 5Kg/cmExample-1 Example-2

Molecular Weight:123.15
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:123.068413911
Monoisotopic Mass:123.068413911
Topological Polar Surface Area:46.2
Heavy Atom Count:9
Complexity:77
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes