Hydrochloric Acid → (Quinolin-8-yloxy)-acetic acid

Temperature

80 °C

To a stirred mixture of quinolin-8-ol (500 mg, 3.45 mmol) in MeCN (5 mL) was added ethyl bromoacetate (687 mg, 4.14 mmol) and K2CO3 (952 mg, 6.90 mmol). The mixture was stirred at 80° C. for 4 hours until TLC analysis showed completion of the reaction. The mixture was filtered and the filtrate concentrated. NaOH (276 mg, 6.90 mmol) and water:EtOH (1:1, 10 mL) was then added to the residue and the resulting mixture stirred at 50° C. for 4 hours. After cooling, the mixture was acidified by addition of 1M HCl to pH 3 and then extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated to yield the crude target product which was used directly for the next step.

1. customcompletion of the reaction
2. filtrationThe mixture was filtered
3. concentrationthe filtrate concentrated
4. stirringthe resulting mixture stirred at 50° C. for 4 hours
5. temperatureAfter cooling
6. extractionextracted with ethyl acetate (2×30 mL)
7. washThe combined organic layers were washed with brine (30 mL)
8. dry with materialdried over anhydrous Na2SO4
9. concentrationconcentrated
10. customto yield the crude target product which

ORD record

ord-4e1031a94092443cb2cddd1e4c0d5b7d

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266836B2