Sodium Hydroxide → 4-Oxo-5-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylic acid

HRID 2404846Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]([C:18]([F:21])([F:20])[F:19])=[C:6]2[C:11]=1[NH:10][CH:9]=[C:8]([C:12]([O:14]CC)=[O:13])[C:7]2=[O:17].[OH-].[Na+]>[Pd].C(O)C>[O:17]=[C:7]1[C:6]2[C:11](=[CH:2][CH:3]=[CH:4][C:5]=2[C:18]([F:21])([F:19])[F:20])[NH:10][CH:9]=[C:8]1[C:12]([OH:14])=[O:13]

Participants

Conditions

Temperature: 50 °C

Procedure

Ethyl 8-chloro-4-oxo-5-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate (500 mg, 1.56 mmol) was dissolved in NaOH (16 mL of 2.0 M, 31 mmol) and ethanol (3 mL) and heated to 100° C. for 2 h. The clear, light yellow solution was cooled to 50° C., the reaction mixture was degassed with N2, and then treated with 10% Pd/C (65 mg, 0.03 mmol). The reaction mixture was heated at 70° C. for 3 h under an atmosphere of H2. The reaction mixture was cooled and then filtered, acidified with conc. HCl until a white precipitate was formed, then allowed to stir overnight. The reaction mixture was filtered, washed with water and dried with CH3CN to yield a white powder (350 mg, 87%). 1H NMR (400 MHz, DMSO-d6) δ 15.26 (s, 1H), 13.68 (s, 1H), 8.98 (s, 1H), 8.16-8.09 (m, 1H), 8.08-7.97 (m, 2H).

Workup

customthe reaction mixture was degassed with N2
temperatureThe reaction mixture was heated at 70° C. for 3 h under an atmosphere of H2
temperatureThe reaction mixture was cooled
filtrationfiltered
customwas formed
filtrationThe reaction mixture was filtered
washwashed with water
dry with materialdried with CH3CN

Sources & evidence

ORD record: ord-ffc2d087cdde44789bceca68e33ac1ba
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802700B2

Reaction notes

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