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

HRID 369274Notes

Reaction equation

[NH2:1][C:2]1[C:3]([F:26])=[CH:4][C:5]([F:25])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15](F)[C:16]=3[Cl:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[CH:7]=1.[CH2:27]([CH2:29][NH2:30])[OH:28].C(N(CC)CC)C>N1C=CC=CC=1>[NH2:1][C:2]1[C:3]([F:26])=[CH:4][C:5]([F:25])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15]([NH:30][CH2:29][CH2:27][OH:28])[C:16]=3[Cl:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

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.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
concentrationA process of adding ethanol (3 ml) to the residue and then concentrating the mixture under reduced pressure
additionEthanol (1 ml) was added to the resultant residue, and deposits
filtrationwere collected by filtration
washwashed with ethanol and diisopropyl ether in that order

Sources & evidence

ORD record: ord-def0dc5aeb1044e084817f793e08ce1e
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136823

Reaction notes

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