ChemicalBook CAS DataBase List 1-CYCLOPROPYL-7-FLUORO-1,4-DIHYDRO-8-METHOXY-4-OXO-3-QUINOLINECARBOXYLIC ACID, ETHYL ESTER

1-CYCLOPROPYL-7-FLUORO-1,4-DIHYDRO-8-METHOXY-4-OXO-3-QUINOLINECARBOXYLIC ACID, ETHYL ESTER synthesis

12synthesis methods

Product Name:1-CYCLOPROPYL-7-FLUORO-1,4-DIHYDRO-8-METHOXY-4-OXO-3-QUINOLINECARBOXYLIC ACID, ETHYL ESTER
CAS Number:221221-15-4
Molecular formula:C16H16FNO4
Molecular Weight:305.3

Benzenepropanoic acid, α-[(cyclopropylamino)methylene]-2,4-difluoro-3-methoxy-β-oxo-, ethyl ester, (αZ)-

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Benzenepropanoic acid, α-[(cyclopropylamino)methylene]-2-ethoxy-4-fluoro-3-methoxy-β-oxo-, ethyl ester, (αZ)-

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10416-59-8
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$18.00/5g

1-CYCLOPROPYL-7-FLUORO-1,4-DIHYDRO-8-METHOXY-4-OXO-3-QUINOLINECARBOXYLIC ACID, ETHYL ESTER

221221-15-4
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Yield:221221-15-4 82%

Reaction Conditions:

in toluene at 105 - 115; for 0.5 h;

Steps:

1.B

Intermediate (18): A reactor is charged with a solution of the mixture of intermediate (17a,b) (4.7 Kg, 3.0 mol) at ambient temperature. To the reactor is added N,O-bis(trimethylsilyl)acetamide (0.61 Kg, 3.0 mol, 1.0 eq) and the reaction is heated to reflux temperature (105-115° C.) for at least 30 minutes or until complete as determined by HPLC analysis. If not complete, an additional amount of N,O-bis(trimethylsilyl)acetamide (0.18 Kg, 0.9 mol, 0.3 eq) is added to the reaction to achieve completion. Upon completion, the reaction is cooled to below 40° C. and organic solvent is removed under reduced pressure (<100 mbar) at approximately 40° C. by distillation until a precipitate is formed. The reaction is cooled to ambient temperature and the precipitated solids are isolated by suction filtration and washed with distilled water twice (1×1.8 L, 1×0.9 L). The solid is dried to afford intermediate (18) as a white solid (0.76 Kg, 82%). The material is used without further purification in the next reaction step.

References:

US2007/232650,2007,A1 Location in patent:Page/Page column 8-9

951313-24-9
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951313-27-2
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221221-15-4
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References