Water → 7,8,9-Trifluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

HRID 1073625Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:7](=[O:24])[C:8]2[CH:9]=[C:10]3[CH:20]=[C:19]([F:21])[C:18]([F:22])=[C:17]([F:23])[C:11]3=[N:12][C:13]=2[N:14]([CH3:16])[CH:15]=1)=[O:5])C.O>C(O)(=O)C.Cl>[F:21][C:19]1[C:18]([F:22])=[C:17]([F:23])[C:11]2=[N:12][C:13]3[N:14]([CH3:16])[CH:15]=[C:6]([C:4]([OH:5])=[O:3])[C:7](=[O:24])[C:8]=3[CH:9]=[C:10]2[CH:20]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A suspension of 4 g of 3-ethoxycarbonyl-7,8,9-trifluoro-1-methyl-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine in 30 cm3 of acetic acid and 30 cm3 of 50% hydrochloric acid is heated at a temperature close to 100° C. for 2 hours. After cooling to about 20° C., 100 cm3 of water are added. The precipitate formed is drained, washed with 3 times 50 cm3 of water and recrystallized from 80 cm3 of dimethylformamide. 3.4 g of 7,8,9-trifluoro-1-methyl-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid are obtained in the form of a colourless solid melting at 350°-352° C.

Workup

temperatureis heated at a temperature
customclose to 100° C. for 2 hours
customThe precipitate formed
washwashed with 3 times 50 cm3 of water
customrecrystallized from 80 cm3 of dimethylformamide

Sources & evidence

ORD record: ord-ee83efbd99de4644a6d49230da47c58c
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04970213

Reaction notes

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