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

HRID 369276Notes

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.[NH2:27][CH:28]([CH3:31])[CH2:29][OH:30].Cl>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:27][CH:28]([CH3:31])[CH2:29][OH:30])[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) and 2-amino-1-propanol (200 mg) were added to pyridine (700 mg), and the mixture was stirred at 50° C. for 1.5 hours. Concentrated hydrochloric acid (200 mg) was added to the reaction mixture, and the resultant mixture was concentrated under reduced pressure. Ethanol (3 ml) was added to the residue, and deposits were collected by filtration and washed with ethanol and disopropyl ether in that order to obtain the title compound (167 mg) as a yellow powder.

Workup

concentrationthe resultant mixture was concentrated under reduced pressure
additionEthanol (3 ml) was added to the residue, and deposits
filtrationwere collected by filtration
washwashed with ethanol and disopropyl ether in that order

Sources & evidence

ORD record: ord-e8b46cfcac8a49878c072d717252cf16
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136823

Reaction notes

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