Water → RP60556A

HRID 1266157Notes

Reaction equation

[F:1][C:2]1[C:22]([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[CH2:25][CH2:24]2)=[CH:21][C:5]2=[N:6][C:7]3[N:8]([CH3:20])[CH:9]=[C:10]([C:15]([O:17]CC)=[O:16])[C:11](=[O:14])[C:12]=3[CH:13]=[C:4]2[CH:3]=1.O>C(O)(=O)C.Cl>[F:1][C:2]1[C:22]([N:23]2[CH2:24][CH2:25][N:26]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[CH2:27][CH2:28]2)=[CH:21][C:5]2=[N:6][C:7]3[N:8]([CH3:20])[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11](=[O:14])[C:12]=3[CH:13]=[C:4]2[CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A suspension of 10.5 g of ethyl 7-fluoro-8-[4-(4-fluorophenyl)piperazin-1-yl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate in 100 cm3 of acetic acid and 100 cm3 of 17.5% aqueous hydrochloric acid solution was heated, with stirring, at a temperature around 110° C. for approximately 4 hours. After cooling to approximately 20° C., 25 cm3 of water were added to the reaction mixture. The insoluble material was filtered off and washed 3 times with 200 cm3 of water and 2 times with 100 cm3 of ethanol. 9.3 g of 7-fluoro-8-[4-(4-fluorophenyl)piperazin-1-yl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid were obtained in the form of a yellow solid melting at approximately 320° C., which solid was used without additional purification in the subsequent stages.

Workup

temperaturewas heated
temperatureAfter cooling to approximately 20° C.
filtrationThe insoluble material was filtered off
washwashed 3 times with 200 cm3 of water and 2 times with 100 cm3 of ethanol

Sources & evidence

ORD record: ord-831f62482b7e459c8ecac633c87c30e7
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06548506B2

Reaction notes

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