Morpholine → 1-Cyclopropyl-6-fluoro-8-methoxy-7-morpholino-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 358863Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH:7]1([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:23])=[C:17](F)[C:18]=3[O:20][CH3:21])[C:13](=[O:24])[C:12]([C:25]([OH:27])=[O:26])=[CH:11]2)[CH2:9][CH2:8]1>CS(C)=O>[CH:7]1([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:23])=[C:17]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)[C:18]=3[O:20][CH3:21])[C:13](=[O:24])[C:12]([C:25]([OH:27])=[O:26])=[CH:11]2)[CH2:8][CH2:9]1

Participants

Conditions

Temperature: 70 °C

Procedure

1.2 g (0.012 mole) of morpholine was added to a solution of 0.9 g (0.003 mole) of 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (IIc) (prepared as described in Preparation 6) in 5 ml of dimethyl sulfoxide, and the mixture was stirred at 70° C. for 6 hours. At the end of this time, the solvent and the excess morpholine were removed at the same temperature by evaporation under reduced pressure. The residue was washed with ethyl acetate and then subjected to silica gel column chromatography eluted with methanol, to afford 0.65 g of 1-cyclopropyl-6-fluoro-8-methoxy-7-morpholino-1,4-dihydro-4-oxoquinoline-3-carboxylic acid as a pale brown powder melting at 235°-237° C.

Workup

customAt the end of this time, the solvent and the excess morpholine were removed at the same temperature by evaporation under reduced pressure
washThe residue was washed with ethyl acetate
washeluted with methanol

Sources & evidence

ORD record: ord-daa520e65f254106bd492e63d0fccce7
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04997943

Reaction notes

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