Toluene → Quinoline

HRID 1416665Notes

Reaction equation

HRID 1416665 reaction equation
CN1CCNCC1.CO[CH:10](OC)[N:11]([CH3:13])C.NC(C)CO.[F-].[K+].[C:23]1([CH3:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)C.CN(C=O)C>[N:11]1[C:10]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:29][CH:13]=1

Participants

8

Reactant 5

HCID 1140TolueneHCID 51262-AminopropanolHCID 531671-MethylpiperazineHCID 78373Dimethylformamide dimethyl acetalHCID 522689Potassium Fluoride

Product 1

HCID 7047Quinoline

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

N-methylpiperazine was first introduced into compound XXXXVIII which was converted to enaminoketoester L on treatment with N,N-dimethylformamide dimethyl acetal in toluene followed by the reaction with 2-amino-1-propanol in ethanol. Reaction of enaminoketoester L with potassium fluoride in DMF gave quinoline LI which was cyclized with strong base such as sodium hydride to give the ester LII. Alternatively, enaminoketoester L may be reacted with sodium hydride in dioxane to yield the ester LII which was hydrolyzed with sodium hydroxide to give Ofloxacin.

Sources & evidence

ORD record
ord-c09fcb6f2693460a88db17837dac6f04
Source dataset
uspto-grants-1999_06
Patent number
US05914401

Reaction notes

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