Phthalaldehyde → 7-Fluoro-8-(4-phthalidyl-1-piperazinyl)-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)-quinoline-4-carboxylic acid

HRID 2295728Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[N:8]1[CH2:18][CH2:19][S:20][C:7]1=[C:6]([C:21]([OH:23])=[O:22])[C:5]2=[O:24].[CH:25]1[CH:30]=[C:29]([CH:31]=[O:32])[C:28]([CH:33]=[O:34])=[CH:27][CH:26]=1>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([CH:31]3[C:29]4[C:28](=[CH:27][CH:26]=[CH:25][CH:30]=4)[C:33](=[O:34])[O:32]3)[CH2:14][CH2:13]1)[N:8]1[CH2:18][CH2:19][S:20][C:7]1=[C:6]([C:21]([OH:23])=[O:22])[C:5]2=[O:24]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 300 mg (0.9 mmol) of 7-fluoro-8-(1-piperazinyl)-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)-quinoline-4-carboxylic acid and 13.5 mg (0.9 mmol) of o-phthal aldehyde acid was suspended in 4 ml of dimethyl formamide and the whole mixture was heated with stirring at 120° C. for seven hours in an oil bath. When the reaction was completed, the mixture was allowed to cool to room temperature and, by collecting the crystals separated out therefrom by filtration, the title compound was obtained as powder. Yield 207 mg (47.7 percent). Melting point 261° to 262° C. (decomposition). Elementary analysis calculated as C24H20FN3O5S: C 59.87, H 4.19, N 8.73; Found: C 60.09, H 4.32, N 8.64.

Workup

temperaturethe whole mixture was heated
temperatureto cool to room temperature
customby collecting the crystals
customseparated out
filtrationby filtration

Sources & evidence

ORD record: ord-d85aa68c66044523827de99f139c4860
Source dataset: uspto-grants-1984_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04426381

Reaction notes

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