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

HRID 743660Notes

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>Cl.C(O)(=O)C>[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: 100 °C

Procedure

A suspension of 0.88 g of 3-ethoxycarbonyl-7,8,9-trifluoro-1-methyl-4-oxo-1,4-dihydrobenzo-[b][1,8]naphthyridine in a mixture of 10 cm3 of 17.5% aqueous hydrochloric acid solution and 10 cm3 of acetic acid is heated with stirring to a temperature in the region of 100° C. for 3 hours. After cooling to approximately 20° C., the product is drained and washed with 3 times 10 cm3 of water. 0.75 g of 7,8,9-trifluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3carboxylic acid is obtained in the form of a pale yellow solid, which decomposes at 352° C. and which is used without further purification for the subsequent steps.

Workup

temperatureis heated
temperatureAfter cooling to approximately 20° C.
washwashed with 3 times 10 cm3 of water

Sources & evidence

ORD record: ord-6f56098e7f87448cb26483e4e2d65b9c
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05556861

Reaction notes

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