Morpholine → 1-Cyclopropyl-6,8-difluoro-7-(morpholin-4-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1710183Notes

Reaction equation

[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.N12CCC(CC1)CN2>CS(C)=O>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 2.83 g (0.01 mol) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 0.9 g (0.01 mol) of morpholine and 2.3 g of diazabicyclo[2.2.2]octane (0.02 mol) in 35 ml of dimethyl sulphoxide is heated to 140° C. for 5 hours. The solvent is distilled off in vacuo, 50 ml of water are added to the residue, the mixture is acidified with semiconcentrated hydrochloric acid, and, when the mixture is cold, the product is filtered off under suction, washed with water, dried in vacuo and recrystallised from glycol monomethyl ether. 2.4 g of 1-cyclopropyl-6,8-difluoro-7-(morpholin4-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid having a decomposition temperature of 257°-260° C. are obtained.

Workup

distillationThe solvent is distilled off in vacuo, 50 ml of water
additionare added to the residue
filtrationthe product is filtered off under suction
washwashed with water
customdried in vacuo
customrecrystallised from glycol monomethyl ether

Sources & evidence

ORD record: ord-a13cf8f3681449b895c879533ff9af8f
Source dataset: uspto-grants-1990_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04952695

Reaction notes

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