Sodium Hydroxide → 2-(2-oxo-7-(trifluoromethoxy)quinolin-1(2H)-yl)acetic acid

HRID 1519797Notes

Reaction equation

[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:7][CH:8]=2)[N:3]1[CH2:17][C:18]([O:20]C)=[O:19].[OH-].[Na+]>C1COCC1.C(OCC)(=O)C>[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([O:12][C:13]([F:15])([F:14])[F:16])=[CH:7][CH:8]=2)[N:3]1[CH2:17][C:18]([OH:20])=[O:19]

Participants

Conditions

Temperature: 60 °C

Procedure

Methyl 2-(2-oxo-7-(trifluoromethoxy)quinolin-1(2H)-yl)acetate (0.49 g, 1.62 mmol) was dissolved in THF (4 mL). Sodium hydroxide (1.08 mL of a 3 N aqueous solution, 3.25 mmol) was added and the reaction mixture was stirred 60° C. for 2 h. The resulting solution was diluted with ethyl acetate and washed with water. The aqueous phase was separated, adjusted to pH 2 with aqueous HCl and extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), filtered and concentrated under vacuum to give 2-(2-oxo-7-(trifluoromethoxy)quinolin-1(2H)-yl)acetic acid. Retention time (min)=1.75, method [1], MS(ESI) 288.1 (M+H).

Workup

washwashed with water
customThe aqueous phase was separated
extractionextracted with ethyl acetate
customThe organic phase was separated
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-ce2867f9d5594419965e31dca8643881
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073891B2

Reaction notes

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