3-Aminobenzyl alcohol

General procedure: In a round-bottomed flask (10 mL) equipped with a magneticstirrer, a mixture of nitrobenzene (0.123 g, 1 mmol)and H2O (2 mL) was prepared. Ni2B (0.006 g, 0.05 mmol) was then added and the mixture was stirred for 5 min.NaBH4 (0.095 g, 2.5 mmol) was also added and the resultingmixture was continued to stirring for 3 min at roomtemperature. TLC monitored the progress of the reaction(eluent, n-hexane/Et2O:5/3). After completion of the reaction, aqueous solution of KOH (2 percent, 5 mL) was addedand the mixture was stirred for 10 min. The mixture wasextracted with EtOAc (3 × 8 mL) and then dried overanhydrous Na2SO4. Evaporation of the solvent affords thepure liquid aniline in 95 percent yield (0.088 g, Table 2, entry 1).General procedure: In a round-bottom flask (10 mL) equipped with a magneticstirrer, a mixture of nitrobenzene (0.123 g, 1 mmol)and H2O (2 mL) was prepared. Cu NPs (0.0095 g, 15 mmol percent) was then added, and the mixture was stirredfor 3 min at 80 °C. Afterward, NaBH4 (0.076 g, 2 mmol)was added portion wisely (two portions) with the intervalof 2 min, and the resulting mixture was continued to stirringat 80 °C. TLC monitored the progress of the reaction(n-hexane/EtOAc: 5/2). After completion of the reaction, Cu NPs was separated by filtration, and the mixture wasextracted with EtOAc (2 × 5 mL). The organic layer wasthen dried over anhydrous Na2SO4. Evaporation of the solventaffords the pure liquid aniline in 91 percent yield (0.085 g, Table 2, entry 1).General procedure: In a round-bottom flask (10 mL) containing 2 mL water, a mixture of nitrobenzene (0.123 g, 1 mmol) and Fe3O4SiO2Cu–Ni–Fe–Cr LDH (10 mg) was prepared and the resulting mixture was stirred for 5 min. Next, NaBH4(0.076 g, 2 mmol) was added and the reaction mixture was stirred magnetically for 3 min under oil bath conditions (60–70 °C). TLC monitored the progress of the reaction (eluent, n-hexane/EtOAc: 5/2). After completion of the reduction reaction, the mixture was cooled to the room temperature. EtOAc (3 mL) was then added and the resulting mixture was again stirred for 10 min. The magnetic nanocatalyst was separated by an external magnet followed by extraction with EtOAc (2 × 5 mL). The combined organic layers were dried over anhydrous Na2SO4. Evaporation of the solvent afforded the pure liquid aniline in 95percent yield (Table 2, entry 1).General procedure: In a round-bottom flask (10 mL) equipped with a magneticstirrer, a mixture of nitrobenzene (1 mmol, 0.123 g) and H2O(2 mL) was prepared. FeGeneral procedure: As a representative example, a mixture of nitrobenzene(1 mmol), NiGeneral procedure: In a round-bottomed flask (10 mL) equipped with a magneticstirrer, a mixture of nitrobenzene (0.123 g, 1 mmol)and H2O (2 mL) was prepared. Ni2B (0.006 g, 0.05 mmol) was then added and the mixture was stirred for 5 min.NaBH4 (0.095 g, 2.5 mmol) was also added and the resultingmixture was continued to stirring for 3 min at roomtemperature. TLC monitored the progress of the reaction(eluent, n-hexane/Et2O:5/3). After completion of the reaction, aqueous solution of KOH (2 percent, 5 mL) was addedand the mixture was stirred for 10 min. The mixture wasextracted with EtOAc (3 × 8 mL) and then dried overanhydrous Na2SO4. Evaporation of the solvent affords thepure liquid aniline in 95 percent yield (0.088 g, Table 2, entry 1).General procedure: In a round-bottom flask (10 mL) equipped with a magneticstirrer, a mixture of nitrobenzene (0.123 g, 1 mmol)and H2O (2 mL) was prepared. Cu NPs (0.0095 g, 15 mmol percent) was then added, and the mixture was stirredfor 3 min at 80 °C. Afterward, NaBH4 (0.076 g, 2 mmol)was added portion wisely (two portions) with the intervalof 2 min, and the resulting mixture was continued to stirringat 80 °C. TLC monitored the progress of the reaction(n-hexane/EtOAc: 5/2). After completion of the reaction, Cu NPs was separated by filtration, and the mixture wasextracted with EtOAc (2 × 5 mL). The organic layer wasthen dried over anhydrous Na2SO4. Evaporation of the solventaffords the pure liquid aniline in 91 percent yield (0.085 g, Table 2, entry 1).General procedure: In a round-bottom flask (10 mL) equipped with a magnetic stirrer, a mixture of nitrobenzene (0.123 g, 1 mmol) and HGeneral procedure: In a round-bottom flask (10 mL) containing 2 mL water, a mixture of nitrobenzene (0.123 g, 1 mmol) and Fe3O4SiO2Cu–Ni–Fe–Cr LDH (10 mg) was prepared and the resulting mixture was stirred for 5 min. Next, NaBH4(0.076 g, 2 mmol) was added and the reaction mixture was stirred magnetically for 3 min under oil bath conditions (60–70 °C). TLC monitored the progress of the reaction (eluent, n-hexane/EtOAc: 5/2). After completion of the reduction reaction, the mixture was cooled to the room temperature. EtOAc (3 mL) was then added and the resulting mixture was again stirred for 10 min. The magnetic nanocatalyst was separated by an external magnet followed by extraction with EtOAc (2 × 5 mL). The combined organic layers were dried over anhydrous Na2SO4. Evaporation of the solvent afforded the pure liquid aniline in 95percent yield (Table 2, entry 1).General procedure: To a sealed tube containing the nitro compound (0.6 mmol) and 2 mL ethanol were added 2.6–6.0 mmol of NHGeneral procedure: In an 8mL glass vial fitted with a magnetic stirring bar and a septum cap, the catalyst (the amount depends on the catalyst) was added followed by the nitroarene (0.5mmol), the internal standard (hexadecane, 20mg) and the solvent (2mL). A needle was inserted in the septum cap, which allows dihydrogen to enter. The vials (up to 7) were placed into a 300mL steel Parr autoclave which was flushed twice with dihydrogen at 20bar and then pressurized to 50bar. Then the autoclave was placed into an aluminum block pre-heated at 110°C. At the end of the reaction, the autoclave was quickly cooled down at room temperature with an ice bath and vented. Finally, the samples were removed from the autoclave, diluted with a suitable solvent, filtered using a Pasteur pipette filled with Celite® (6cm pad) and analyzed by GC using n-hexadecane as an internal standard. Control experiments showed that the position of the vial inside the autoclave is not influential. The same outcome was obtained when the reaction was repeated by moving a vial from a peripheral to a central position.Lithium aluminum hydride (1.0 M in THF, 29.9 mL, 29.9 mmol) was added slowly to a solution of 3-cyanobenzaldehyde (1.12 g, 9.25 mmol) in anhydrous THF (25.0 mL) at room temperature under argon and the mixture was stirred at reflux (overnight). The reaction mixture was cooled to room temperature and quenched by addition of ice and NaOH (aq. 3.0 N, 10.0 mL). The mixture was extracted with chloroform (3 x 80 mL) and the combined organic phase was washed with brine (2 x 20 mL) and dried (Na

Molecular Weight:123.15
XLogP3:-0.1
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:85
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes