Triethylamine → Ethyl 4-oxo-5-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate

HRID 1879326Notes

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][CH2:15][CH3:16])=[O:13])[C:7]2=[O:17].C(N(CC)CC)C>[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:19])([F:20])[F:21])[NH:10][CH:9]=[C:8]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

Conditions

Temperature: 5 °C

Procedure

A 3-neck, 5-L flask was charged with of ethyl 8-chloro-4-oxo-5-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate 15 (100 g, 0.3 mol), ethanol (1250 mL, 12.5 mL/g) and triethylamine (220 mL, 1.6 mol). The vessel was then charged with 10 g of 10% Pd/C (50% wet) at 5° C. The reaction was stirred vigorously under hydrogen atmosphere for 20 h at 5° C., after which time the reaction mixture was concentrated to a volume of approximately 150 mL. The product, ethyl 4-oxo-5-(trifluoromethyl)-1H-quinoline-3-carboxylate 16, as a slurry with Pd/C, was taken directly into the next step.

Workup

concentrationafter which time the reaction mixture was concentrated to a volume of approximately 150 mL

Sources & evidence

ORD record: ord-195635d92d9c408aba8ed8efb3ec7cc2
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314239B2

Reaction notes

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