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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1589566Generated: October 26, 2026

1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-(2,5-Diazabicyclo[2.2.2]oct-2-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

https://huagongshe.com/reaction/1589566

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
Reactant1-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 535414—
Reactant2,5-Diazabicyclo(2.2.2)octane dihydrochlorideHCID 22924390—
SolventAcetonitrileHCID 6342—
Product7-(2,5-Diazabicyclo[2.2.2]oct-2-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidHCID 1356579471.9%

Reaction Steps

A mixture of 0.28 g (1 mmole) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 0.2 g (1.1 mmole) 2,5-diazabicyclo[2.2.2]octane dihydrochloride [P. A. Sturm et al., J. Med. Chem., 17, 481 (1974)], 0.45 ml (3.0 mmole) of 1,8-diazabicyclo[5.4.0]undec-7-ene and 10 ml of acetonitrile was heated at reflux for four hours. After cooling to room temperature, the reaction mixture was filtered and the solid washed with ethanol and dried to give 0.27 g of the title compound, mp 275°-280° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04571396
Source datasetuspto-grants-1986_02
ORD IDord-b4480c4ece6d468c8636cf4ad1cee364
Source noteuspto-grants-1986_02