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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 369274Generated: October 28, 2026

Ethanolamine → 1-(5-Amino-2,4-difluorophenyl)-8-chloro-6-fluoro-7-(2-hydroxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

https://huagongshe.com/reaction/369274

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthanolamineHCID 700—
ReactantTriethylamineHCID 8471—
Reactant1-(3-Amino-4,6-difluorophenyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 10861999—
SolventPyridineHCID 1049—
Product1-(5-Amino-2,4-difluorophenyl)-8-chloro-6-fluoro-7-(2-hydroxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic AcidHCID 2328468985%

Reaction Conditions

Temperature50 °C

Reaction Steps

1-(5-Amino-2,4-difluorophenyl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (200 mg), ethanolamine (35 mg) and triethylamine (200 mg) were added to pyridine (600 mg), and the mixture was stirred at 50° C. for 15.5 hours. The reaction mixture was concentrated under reduced pressure. A process of adding ethanol (3 ml) to the residue and then concentrating the mixture under reduced pressure was conducted twice repeatedly. Ethanol (1 ml) was added to the resultant residue, and deposits were collected by filtration and washed with ethanol and diisopropyl ether in that order to obtain the title compound (188 mg) as a pale brown powder.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06136823
Source datasetuspto-grants-2000_10
ORD IDord-def0dc5aeb1044e084817f793e08ce1e
Source noteuspto-grants-2000_10