Acetic Anhydride → Ethyl 6-fluoro-7-(pyrrol-1-yl)-1-formylamino-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 4566

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1)[N:8]([NH2:17])[CH:7]=[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:5]2=[O:23].[C:24](OC(=O)C)(=[O:26])C>C(O)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16]1)[N:8]([NH:17][CH:24]=[O:26])[CH:7]=[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:5]2=[O:23]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3.15 g (0.01 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-1-amino-4-oxo-1,4-dihydroquinoline-3-carboxylate in 25 ml of formic acid is added dropwise to a mixture of 9.5 ml (0.01 mol) of acetic anhydride and 4 ml (0.01 mol) of formic acid, cooled to 0° C., the addition being carried out so as to maintain room temperature ±5° C. The mixture is kept at room temperature for48 hours and poured into a water/ice mixture, and the precipitate formed is filtered off, washed with water and recrystallized from a dimethylformamide/water mixture (1:1) to give a solid melting at 254°-257° C.

Workup

additionthe addition
temperatureto maintain room temperature ±5° C
waitThe mixture is kept at room temperature for48 hours
customthe precipitate formed
filtrationis filtered off
washwashed with water
customrecrystallized from a dimethylformamide/water mixture (1:1)

Sources & evidence

ORD record: ord-8adc3019916d41df93e9978debdaa4cb
Source dataset: uspto-grants-1988_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04727080

Linked notes

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