Analyzing the synthesis route of 2-(2-Aminophenyl)ethanol

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5339-85-5, 2-(2-Aminophenyl)ethanol, and friends who are interested can also refer to it.

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.5339-85-5, name is 2-(2-Aminophenyl)ethanol, molecular formula is C8H11NO, molecular weight is 137.18, as common compound, the synthetic route is as follows.Quality Control of 2-(2-Aminophenyl)ethanol

A 250 mL 3 -neck round-bottom flask equipped with mechanical stirrer and a temperature -probe was set up under N2. Ethyl acetetate (45 mL) and 2-aminophenethanol (2.0 g, 0.015 mol, purchased from Combi- Blocks Inc, San Diego, CA) were added and stirred well in a ice bath cooled to 0 to 5 C. A homogeneous clear solution of K2C03 in water (45 mL) was added in one portion. To a vigorously stirring solution was added acryloyl chloride (0.7 g, 0.007 mol, Sigma Aldrich) carefully in portions with a syringe at a rate that maintains the temperature below 5oC. To the resulting solution was added BHT (0.004 g, 0.018 mmol). After 4 hours, reaction progress was monitored by silica gel TLC (50:50 DCM:EtOAc eluent). Product: f=~0.5 (UV-active). The starting material was not observed. The reaction mixture then was diluted with ethyl acetate (100 mL), transferred to a separatory funnel, and washed with IN HCI (50 mL), sat. aq. NaHC03 (50 mL.), brine (50 mL), dried (Na2S04), filtered, and concentrated on a rotovap to obtain a white solid that was further dried under high, vacuum. 1H NMR (400 MHz, Acetone-d6). d (ppm) 9.64 (br, IH), 7.93 (d, 1H), 7.20 (m, 2H), 7.02 (dd, IH), 6.33 (m, 2H), 5.70 (d, IH), 4.71 (s, 1 H), 3.86 (dd, 2H), 2.86 (dd, 2H). This product was used without further purification in the next step of sy nthesis.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5339-85-5, 2-(2-Aminophenyl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; SNAP BIO, INC.; BURK, Mark J.; CHEN, Brandon; LI, Jingyi; BACHAN, Shawn; (161 pag.)WO2019/67396; (2019); A1;,
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