2-Aminoresorcinol

2-nitrobenzene-1, 3-diol (1.00 g, 6.5 mmol)Of ethanol (20 ml)Palladium on carbon in the solution (200 mg)It was added at 0 under an argon atmosphere.After hydrogen substitution, and stirred at room temperature for 4 hours.After completion of the reaction, it was filtered through Celite, and the filtrate was concentrated under reduced pressure, to give the title compound (827 mg, 100percent).The mixture of 2-nitroresorcinol (250 mg, 1.61 mmol) and 10percent Pd/C (25 mg) inethanol (5 mL) was hydrogenated under an atmosphere of hydrogen (1 atm) at roomtemperature overnight. Pd/C was filtered off and the filtrate was concentrated undervacuum to give the title compound as a light yellow solid (201 mg, 100percent) withoutfurther purification; mp 163-165 °C; 1H NMR (300 MHz, DMSO-d6) δ (ppm) 8.80(brs, 2H), 6.29-6.20 (m, 3H), 3.84 (brs, 2H); HRMS (ESI): m/z, Calcd. for C6H8O2N[M+H]+: 126.0550, Found 126.0552.Example 3 5{[(2S)-3-(5-Chloro-1'H, 3H-spiro[1-benzofuran-2, 4'-ipiperidin]-1'-yl)-2- hydroxypropyl] oxy}-2H-1, 4-benzoxazin-3 (4R)-one Step I : 2-Aminobenzene-1, 3-diol A mixture of 2-nitrobenzene-1, 3-diol (5 g, 32.2 mmol) and 10percent Pd on charcoal (230 mg) in ethanol (100 ml) were hydrogenated with H2 at atmospheric pressure overnight. The reaction mixture was filtered through celite. Ethanol was removed by evaporation to yield the subtitled compound (4 g, 99percent). 'H-NMR (400 MHz, DMSO-d6) : 8 8.81 (br. s, 2H), 6.24 (m, 3H), 3.81 (br. s, 2H). APCI-MS: m/z 126.0 (MHF).(1) A solution of 2-nitrobenzene-l, 3-diol (5.00 g, 32.2 mmol) in MeOH (100 mL) was stirred under Hλ/thermometer, Cooling pipe, 500 mL equipped with a stirrerIn a flask, 25.50 g (0.164 mol) of 2-nitroresorcinol manufactured by Tokyo Chemical Industry Co., Ltd., 2.60 g of 10percent palladium on carbon (Pd / C)And methanol (320 mL), and the mixture was stirred at room temperature.Under a hydrogen atmosphere, Hydrogen reduction reaction was carried out at room temperature for 36 hours.After filtering the reaction solution, The filtrate was concentrated under reduced pressure, Followed by vacuum drying at 80 ° C. for 12 hours to obtain 20.22 g of a crude product.The obtained crude product was separated and purified by silica gel column chromatography (developing solvent: ethyl acetate / hexane = 2/1, volume ratio)16.60 g (yield 80.9percent) of 2, 6-dihydroxyaniline was obtained.General 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.a) [0338] 465 mg of 2-nitroresorcinol was dissolved in 9.3 ml of ethanol, 230 mg of 10percent palladium/carbon was added, followed by stirring under a hydrogen atmosphere at room temperature for 1 hour. The insoluble material was filtered and subsequently the solvent was distilled off under reduced pressure to afford 338.5 mg of the title compound. [0339] a) 2-Aminobenzene-1, 3-diol [0219] 465 mg of 2-nitroresorcinol was dissolved in 9.3 ml of ethanol, 230 mg of 10percent palladium/ carbon was added, followed by stirring under a hydrogen atmosphere at room temperature for 1 hour. The insoluble material was filtered and subsequently the solvent was distilled off under reduced pressure to afford 338.5 mg of the title compound. 465 mg of 2-nitroresorcinol was dissolved in 9.3 ml of ethanol, 230 mg of 10percent palladium/carbon was added, followed by stirring under a hydrogen atmosphere at room temperature for 1 hour. The insoluble material was filtered and subsequently the solvent was distilled off under reduced pressure to afford 338.5 mg of the title compound. 465 mg of 2-nitroresorcinol was dissolved in 9.3 ml of ethanol, 230 mg of 10percent palladium/ carbon was added, followed by stirring under a hydrogen atmosphere at room temperature for 1 hour. The insoluble material was filtered and subsequently the solvent was distilled off under reduced pressure to afford 338.5 mg of the title compound. [0369]

Molecular Weight:125.13
XLogP3:0.5
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Exact Mass:125.047678466
Monoisotopic Mass:125.047678466
Topological Polar Surface Area:66.5
Heavy Atom Count:9
Complexity:87.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes