Methyl iodide → Ethyl 6-fluoro-7-(pyrrol-1-yl)-1-formylmethylamino-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 4567Notes

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]([NH:17]C=O)[CH:7]=[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:5]2=[O:25].[C:26](=[O:29])([O-])[O-].[K+].[K+].[CH3:32]I>CN(C)C=O>[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]([NH:17][CH2:32][CH:26]=[O:29])[CH:7]=[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:5]2=[O:25]

Participants

Conditions

Temperature: 35 °C

Procedure

A mixture of 3.47 g (0.01 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-1-formylamino-4-oxo-1,4-dihydroquinoline-3-carboxylate and 3 g (~0.02 mol) of potassium carbonate in 25 ml of dimethylformamide is heated for 10 minutes at 35° C. It is kept at room temperature for 2 hours in a partially precipitated state, 4.3 g (0.03 mol) of methyl iodide are added to this suspension and the mixture is kept at room temperature for 3 hours. It is poured into a water/ice mixture, the precipitate formed is filtered off, washed with water and extracted with chloroform, the mixture is filtered, the solution is evaporated and the residue is recrystallized from an ethanol/water mixture (1:1) to give 1.43 g of a solid melting at 194°-198° C.

Workup

additionare added to this suspension
customthe precipitate formed
filtrationis filtered off
washwashed with water
extractionextracted with chloroform
filtrationthe mixture is filtered
customthe solution is evaporated
customthe residue is recrystallized from an ethanol/water mixture (1:1)

Sources & evidence

ORD record: ord-a25eb7b5f55f482ab43f2e9c4ec90170
Source dataset: uspto-grants-1988_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04727080

Reaction notes

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