Potassium Carbonate → Ethyl 1-cyclopropyl-6-fluoro-7-bromo-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 486268Notes

Reaction equation

HRID 486268 reaction equation
[Br:1][C:2]1[CH:20]=[C:19](Br)[C:5]([C:6]([C:8](=[CH:14][NH:15][CH:16]2[CH2:18][CH2:17]2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])=[C:4]([CH3:22])[C:3]=1[F:23].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:16]1([N:15]2[C:19]3[C:5](=[C:4]([CH3:22])[C:3]([F:23])=[C:2]([Br:1])[CH:20]=3)[C:6](=[O:7])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:14]2)[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178418426HCID 178418426, compound

Product 1

HCID 14651283Ethyl 1-cyclopropyl-6-fluoro-7-bromo-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylateYield 91.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture comprising ethyl 2-(4,6-dibromo-3-fluoro-2-methylbenzoyl)-3-cyclopropylaminoacrylate (45.0 g), potassium carbonate (16.7 g) and dimethylformamide (450 ml) is reacted at 140° C. for 30 minutes. After cooling, the reaction mixture is poured into ice-water and the precipitated crystals are filtered, which are recrystallized from ethanol to give ethyl 1-cyclopropyl-6-fluoro-7-bromo-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (33.6 g), as white crystals, m.p. 195°-197° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated crystals are filtered
  3. customwhich are recrystallized from ethanol

Sources & evidence

ORD record
ord-710b96de3f3a4d26a9b07742ad59e1ef
Source dataset
uspto-grants-1994_03
Patent number
US05290934

Reaction notes

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