Citric Acid → HCID 23284740, compound

HRID 369336Notes

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.CO.[NH2:29][CH:30]1[CH2:33][O:32][CH2:31]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>N1C=CC=CC=1.CN1CCCC1=O>[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:29][CH:30]4[CH2:33][O:32][CH2:31]4)[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: 70 °C

Procedure

1-(5-Amino-2,4-difluorophenyl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (100 mg) was dissolved in a mixed liquid of pyridine (0.5 ml) and N-methylpyrrolidone (0.5 ml). A methanol solution (45%; 1.5 ml) of 3-aminooxetane was added to the resultant solution. The mixture was stirred at 70° C. for 18 hours. The reaction mixture was acidified with a 3% aqueous solution (20 ml) of citric acid, and solids formed were collected by filtration. The solids were subjected to azeotropic distillation with ethanol. Ether (5 ml) was added to the residue to conduct filtration, thereby obtaining the title compound (48 mg) as a pale yellow powder.

Workup

customformed
filtrationwere collected by filtration
distillationThe solids were subjected to azeotropic distillation with ethanol
additionEther (5 ml) was added to the residue
filtrationfiltration

Sources & evidence

ORD record: ord-dcb1f1208052441084834103a3ac630f
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136823

Reaction notes

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