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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 434692Generated: October 30, 2026

Morpholine → 9-morpholino-8-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid

https://huagongshe.com/reaction/434692

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMorpholineHCID 8083—
Reactant9-fluoro-8-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acidHCID 13472998—
SolventHexamethylphosphoramideHCID 12679—
Product9-morpholino-8-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acidHCID 1304430220.9%

Reaction Steps

An autoclave containing a mixture of 3 g of 9-fluoro-8-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, 8 g of morpholine and 30 ml of hexamethylphosphoric triamide was immersed in an oil bath at 190° C. and reaction was continued for 5 hours. After completion of reaction, the reaction mixture was cooled to precipitate crystals which then were collected by filtration. The crystals thus obtained were recrystallized from dimethylformamide to give 0.77 g of 9-morpholino-8-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid. m.p. 271° to 274° C., white rhombic crystals.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04399134
Source datasetuspto-grants-1983_08
ORD IDord-8a1faa193dbb4072ad058df1f0dac16e
Source noteuspto-grants-1983_08