Sodium Hydroxide → 2-(quinolin-8-yloxy)propanoic acid

Temperature

27 °C

To a solution of ethyl 2-(quinolin-8-yloxy)propanoate (100 mg, 0.4 mmol) in EtOH (1 ml) was added a solution of NaOH (24 mg, 0.6 mmol) in H2O (0.5 ml) at 27° C. The mixture was stirred for 30 min at 27° C. The mixture was then concentrated and the residue treated with water (5 mL) and extracted with ethyl acetate (2×5 mL). The water layer was then treated with 2N HCl until pH 3 before being extracted with ethyl acetate (2×5 ml). The organic layer was washed with brine (30 mL), dried over Na2SO4 and concentrated to give the title product (70 mg, 80.5%) as a white solid which was used in next step without further purification.

1. concentrationThe mixture was then concentrated
2. additionthe residue treated with water (5 mL)
3. extractionextracted with ethyl acetate (2×5 mL)
4. additionThe water layer was then treated with 2N HCl until pH 3
5. extractionbefore being extracted with ethyl acetate (2×5 ml)
6. washThe organic layer was washed with brine (30 mL)
7. dry with materialdried over Na2SO4
8. concentrationconcentrated

ORD record

ord-670d4439d5a74691a02c5c7a9c446081

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08940726B2