2-Hydroxyquinoline → Acetic benzoic anhydride

HRID 277975Notes

Reaction equation

HRID 277975 reaction equation
N1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=CC1=O.BrC1C=CC(C(Cl)=[O:18])=CC=1F.[K+].C([O:26][C:27](=[O:32])[CH2:28]C([O-])=O)C>>[C:27]([O:32][C:4](=[O:18])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)(=[O:26])[CH3:28]

Participants

4

Reactant 3

HCID 60382-Hydroxyquinoline2×HCID 3446434Potassium ethyl malonateHCID 226268914-Bromo-3-fluorobenzoyl chloride

Product 1

HCID 9548685Acetic benzoic anhydride

Procedure

As an alternative to the quinolone synthesis outlined above, the quinolone nucleus may be formed using the route illustrated in Scheme II. Similar methodology for the preparation of quinolones was first described in German patent application DE3142854. Starting from a 4-bromo-3-fluoro-benzoyl chloride, condensation with malonic acid monoethyl ester monopotassium salt gives a benzoyl acetate that is subsequently reacted with triethyl orthoformate. The resulting ethoxymethylene derivative is reacted with a primary amine and cyclized to the quinolone.

Workup

  1. custommay be formed

Sources & evidence

ORD record
ord-b36636746fe14d5b9b894f1b542b7f16
Source dataset
uspto-grants-2002_03
Patent number
US06358976B1

Reaction notes

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