3-Ethoxycarbonyl-7,8-difluoro-1-ethyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine → HCID 19423693, compound

HRID 981207Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:7](=[O:24])[C:8]2[CH:9]=[C:10]3[CH:21]=[C:20]([F:22])[C:19]([F:23])=[CH:18][C:11]3=[N:12][C:13]=2[N:14]([CH2:16][CH3:17])[CH:15]=1)=[O:5])C>Cl.C(O)(=O)C>[CH2:16]([N:14]1[C:13]2[N:12]=[C:11]3[CH:18]=[C:19]([F:23])[C:20]([F:22])=[CH:21][C:10]3=[CH:9][C:8]=2[C:7](=[O:24])[C:6]([C:4]([OH:5])=[O:3])=[CH:15]1)[CH3:17]

Participants

Conditions

Temperature: 20 °C

Procedure

A suspension of 8 g of 3-ethoxycarbonyl-1-ethyl-7,8-difluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine in 80 cm3 of 17.5% hydrochloric acid and 80 cm3 of acetic acid is heated, with stirring, at a temperature close to 100 hour and 30 minutes. After cooling to about 20° C., the insoluble matter is drained, washed with 3 times 20 cm3 of water and recrystallized from 50 cm3 of dimethylformamide. 6.3 g of 1-ethyl-7,8-difluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid are obtained in the form of a yellow solid melting at 330° C.

Workup

temperatureis heated
customclose to 100 hour and 30 minutes
washwashed with 3 times 20 cm3 of water
customrecrystallized from 50 cm3 of dimethylformamide

Sources & evidence

ORD record: ord-a550295f171443d49d9614bba0eeda4d
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04990515

Reaction notes

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