Acetone → 4-Quinolone-3-carboxylic acid

HRID 1865218Notes

Reaction equation

HRID 1865218 reaction equation
C1([N:4]2[C:13]3[C:8](=[CH:9][C:10](F)=[C:11](Cl)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)CC1.N1CCCCC1.CC(C)=O.N12CCCC1=NCCC2>C(N(CC)CC)C.N1C=CC=CC=1.CS(C)=O.C(#N)C.CN(C)C=O>[O:16]=[C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:4][CH:5]=[C:6]1[C:17]([OH:19])=[O:18]

Participants

10

Reactant 4

HCID 180AcetoneHCID 8082PiperidineHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 483180Fluoroquinolonic acid

Product 1

HCID 2208754-Quinolone-3-carboxylic acid

Reagents, catalysts & solvents 5

HCID 679Dimethyl SulfoxideSolvent2×HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent2×

Procedure

1-Cyclopropyl-6-fluoro-7-{(4-amino/substituted amino /disubstituted amino/hydroxy-3-alkyl/3,3-dialkyl/3,5-dialkyl)1-1-piperidinyl)-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid and isomers were prepared by heating a mixture of 1-cyclopropyl-6-fluoro-7-chloro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid with appropriate {4-(amino/substituted amino/disubstituted amino/hydroxy-3-alkyl/3,3-dialkyl/3,5-dialkyl/3,3,5-trialkyl)}piperidine in an organic solvent optionally in the presence of a base at 50°-120° C., preferably 90° C. for 4-72 hr. The solvent may be selected from acetone, alcohol, acetonitrile, dimethyl sulphoxide, N,N-dimethylformamide preferably acetonitrile or dimethyl sulphoxide. The base may be selected from triethylamine, pyridine, 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), or 1,7-diazabicyclo[5.4.0]undec-7-ene (DBU), preferably triethylamine.

Workup

  1. temperatureby heating

Sources & evidence

ORD record
ord-f350883185ab4fa3bd4faf979f69c4ab
Source dataset
uspto-grants-2009_12
Patent number
US07626032B2

Reaction notes

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