Hydrochloric Acid → 3-carboxy-2-trifluoromethyl-2-hydroxy-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone

HRID 54439

Reaction equation

[C:1]([CH:6]1[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:14]2[C:13](=[O:25])[CH2:12][CH2:11][CH2:10][C:9]=2[NH:8][C:7]1([C:27]([F:30])([F:29])[F:28])[OH:26])([O:3]CC)=[O:2].O.[OH-].[Li+].Cl>C(O)C.O>[C:1]([CH:6]1[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:14]2[C:13](=[O:25])[CH2:12][CH2:11][CH2:10][C:9]=2[NH:8][C:7]1([C:27]([F:30])([F:28])[F:29])[OH:26])([OH:3])=[O:2]

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of 3-carboethoxy-2-trifluoromethyl-2-hydroxy-4-(3-nitrophenyl)-2,3,4,6,7,8-hexahydro-5(1H)-quinolone (7.02 g) in ethanol (40ml) and water (40ml) was treated with lithium hydroxide monohydrate (1.44 g). The mixture was heated at 90° C. for 30 minutes, diluted with water, acidified with 1N hydrochloric acid, and extracted with ethyl acetate. The combined organic extracts were washed (water and brine), dried, filtered and the solvent stripped to yield a brown oil which was further purified by chromatography (ethyl acetate and ethyl acetate/methanol, 4:1). 3-Carboxy-2-trifluoromethyl-2-hydroxy-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone (2.07 g) was obtained as a white solid. NMR: 1.85 (m,2, CH2), 2.10 (m,2, CH2), 2.33-2.60 (m,3, CH2, CH), 4.21 (d,1, J=8.7, CH), 7.47 (m,2, Ar), 7.81 (s,2, OH or NH, Ar), 7.96 (m, 1H, Ar); MS: m/z=400(M).

Workup

extractionextracted with ethyl acetate
washThe combined organic extracts were washed (water and brine)
customdried
filtrationfiltered
customto yield a brown oil which
customwas further purified by chromatography (ethyl acetate and ethyl acetate/methanol, 4:1)

Sources & evidence

ORD record: ord-e44ffa27fb374f98bef38cc0ef1eb098
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05622964

Linked notes

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