3-Amino-2-hydroxyacetophenone

Yellow crystalline powder

The3-acetamido-4-acetoxybenzenesulfonic acid (136 g)Dissolved in 300 ml of nitrobenzene, add anhydrous aluminum trichloride 133g, heated to reflux 5h, after the end of the reaction, vacuum recovery of most of the solvent, cooled to room temperature, Ice bath, the reaction solution slowly added to 30percent dilute hydrochloric acid, room temperature stirring 2h, Slowly heated to reflux, reaction 4h, after the end of the reaction, the reaction solution cooled to room temperature, adding 20percent sodium hydroxide solution to the reaction system to adjust the pH9-10.Add 300 ml of chloroform to extract, washed with water to neutral, dried over anhydrous sodium sulfate, filtered and the filtrate was recovered under reduced pressure. The residue was recrystallized from petroleum ether: ethyl acetate = 1: 3 to give 65.7 g of product as a pale yellow solid.Take 3-acetamido-4-acetoxybenzenesulfonic acid 136g, Dissolved in 300 ml of chloroform, Add 133 g of anhydrous aluminum trichloride, Heated to reflux 5h, after the reaction, Most of the solvent was recovered under reduced pressure, cooled to room temperature, Under ice bath, the reaction mixture was slowly added to 30percent diluted hydrochloric acid, Stirred at room temperature 2h, slowly warmed to reflux, the reaction 4h, after the reaction, The reaction solution was cooled to room temperature, 20percent sodium hydroxide solution was added to the reaction system to adjust pH9-10.Add 300 ml of chloroform extract, washed until neutral, Anhydrous sodium sulfate, filtered, the filtrate was recovered under reduced pressure, The residue was recrystallized from petroleum ether: ethyl acetate = 1: 3 to give a pale yellow solid (65.7 g) in 87percent yield.To the hydrogenation reactor, 114 kg of 2-hydroxy-3-amino-5-bromoacetophenone, 200 kg of absolute ethanol, 6 kg of Pd /C, into the hydrogen, replace the reactor in the air, pressure to 2Mpa, heating reflux reaction 8h. After completion of the reaction, the mixture was cooled to room temperature and the solvent was recovered under reduced pressure. Petroleum ether: ethyl acetate = 1: 3 was recrystallized to give 68 kg of a white solid in 91percent yield.Take 2-acetamidophenol acetate 96kg, Dissolved in 250kg N-methylpyrrolidone, Add anhydrous titanium tetrachloride 94kg, 120 degrees reaction 3h, After the reaction, Decompression recovery most of the solvent, Cool to room temperature, Under ice bath, The reaction solution was slowly added to 30percent diluted hydrochloric acid, Stirred at room temperature for 2h, Slowly warmed to reflux, Reaction 4h, After the reaction, The reaction solution was cooled to room temperature, To the reaction system by adding 20percent sodium hydroxide solution to adjust pH9-10.Add 300kg dichloromethane extraction, Washed to neutral, Dried over anhydrous sodium sulfate, filter, The filtrate was recovered under reduced pressure, The residue was recrystallized from petroleum ether: ethyl acetate = 1: 3 as a light yellow solid, 65.7 kg, Yield 87percent.In a 10 mL reaction tube, a PTFE magnet is placed in a nitrogen atmosphere.Add 0.3 mmol of

Molecular Weight:151.16
XLogP3:1.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:151.063328530
Monoisotopic Mass:151.063328530
Topological Polar Surface Area:63.3
Heavy Atom Count:11
Complexity:158
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes