Hydrochloric Acid → 7-[(2,5-Dioxopyrrolidin-1-yl)methyl]-8-fluoro-4-(4-fluorophenyl)quinoline-2-carboxylic acid

HRID 922800Notes

Reaction equation

Cl.[O:2]=[C:3]1[CH2:7][CH2:6][C:5](=[O:8])[N:4]1[CH2:9][C:10]1[C:19]([F:20])=[C:18]2[C:13]([C:14]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:15][C:16]([C:21]([O:23]C)=[O:22])=[N:17]2)=[CH:12][CH:11]=1>C(O)(=O)C>[O:8]=[C:5]1[CH2:6][CH2:7][C:3](=[O:2])[N:4]1[CH2:9][C:10]1[C:19]([F:20])=[C:18]2[C:13]([C:14]([C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)=[CH:15][C:16]([C:21]([OH:23])=[O:22])=[N:17]2)=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 120 °C

Procedure

6M HCl (2964 μl) was added to a solution of methyl 7-[(2,5-dioxopyrrolidin-1-yl)methyl]-8-fluoro-4-(4-fluorophenyl)quinoline-2-carboxylate 7-11 (629 mg, 1.482 mmol) in Acetic Acid (2964 μl) and the reaction heated at 120° C. for 10 min in the microwave. The reaction was quenched with KH2PO4 (saturated) and the mixture was extracted with ethyl acetate (×3). The combined organic fractions were dried (MgSO4), filtered and the solvent was evaporated under reduced pressure to afford 7-[(2,5-dioxopyrrolidin-1-yl)methyl]-8-fluoro-4-(4-fluorophenyl)quinoline-2-carboxylic acid 7-12 (499 mg, 85% yield) as a white solid, 100% pure by LCMS, LRMS m/z (M+11)+ 397.2 found, 397.1 required.

Workup

customThe reaction was quenched with KH2PO4 (saturated)
extractionthe mixture was extracted with ethyl acetate (×3)
dry with materialThe combined organic fractions were dried (MgSO4)
filtrationfiltered
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-d2a5c6ed2ab743b9955216b749037b4c
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278960B2

Reaction notes

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