Ethyl bromoacetate → [(Quinolin-4-yl)oxy]acetic acid

The mixture of 4-hydroxyquinoline (290 mg, 2.0 mmol), potassium carbonate (910 mg, 6.6 mmol), ethyl bromoacetate (500 mg, 3.0 mmol) and acetone (25 ml) was refluxed for 8 h. After cooling, the mixture was filtered to remove potassium carbonate. The filtrate was concentrated under reduced pressure. To this residue, 10 ml of dioxane and 14 ml 5% sodium hydroxide solution was added. After the mixture was stirred at room temperature overnight, it was acidified with concentrated hydrochloric acid to pH 3, and then extracted three times with ethyl acetate (20 ml each). Water layer was placed in cold room, and solid came out. The crystals were filtered with suction and washed with water, and then dried to give 120 mg quinoline-4-oxyacetic acid as gray crystals, mp 274-276° C.

1. temperaturewas refluxed for 8 h
2. temperatureAfter cooling
3. filtrationthe mixture was filtered
4. customto remove potassium carbonate
5. concentrationThe filtrate was concentrated under reduced pressure
6. additionTo this residue, 10 ml of dioxane and 14 ml 5% sodium hydroxide solution was added
7. extractionextracted three times with ethyl acetate (20 ml each)
8. filtrationThe crystals were filtered with suction
9. washwashed with water
10. customdried

ORD record

ord-4469fc053b264f18bfd07731e0b98434

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06350756B1