Methanol → Methyl 3-(4-aminophenyl)propanoate

SOCl2(1.5 mL) was added slowly to MeOH (6 mL) at 0˜5° C., and the mixture was stirred for 10 minutes. 3-(4-Amino-phenyl)-propionic acid (1 g, 6.05 mmol) was added thereto at the same temperature. After the temperature was elevated to room temperature, the mixture was stirred for 12 hours. After the termination of the reaction, the reactant was concentrated under reduced pressure, added with saturated sodium bicarbonate aqueous solution, and extracted with EtOAc. The organic layer was added with NaCl aqueous solution, extracted again, and then filtered by using celite. The filtrate was concentrated under reduced pressure. The residue was added with n-Hex, and then concentrated under reduced pressure again. n-Hex (20 mL) was added to the obtained solid, and the mixture was stirred under reflux for 1 hour, and then stirred at room temperature for 2 hours. The mixture was filtered to obtain the title compound (0.85 g, 78%).

1. customwas elevated to room temperature
2. stirringthe mixture was stirred for 12 hours
3. customAfter the termination of the reaction
4. concentrationthe reactant was concentrated under reduced pressure
5. additionadded with saturated sodium bicarbonate aqueous solution
6. extractionextracted with EtOAc
7. additionThe organic layer was added with NaCl aqueous solution
8. extractionextracted again
9. filtrationfiltered
10. concentrationThe filtrate was concentrated under reduced pressure
11. additionThe residue was added with n-Hex
12. concentrationconcentrated under reduced pressure again
13. additionn-Hex (20 mL) was added to the obtained solid
14. stirringthe mixture was stirred
15. temperatureunder reflux for 1 hour
16. stirringstirred at room temperature for 2 hours
17. filtrationThe mixture was filtered

ORD record

ord-2c5cf4e5c5d7441f9ac0454ae6a81486

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09447044B2