HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ciprofloxacin → 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-{4-[2-oxo-1-(methoxycarbonyl)-1-propyl]-1-piperazinyl}-3-quinolinecarboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ciprofloxacin | HCID 2764 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methyl 2-chloroacetoacetate | HCID 107332 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-{4-[2-oxo-1-(methoxycarbonyl)-1-propyl]-1-piperazinyl}-3-quinolinecarboxylic acid | HCID 13337931 | 44% |
Reaction Steps
6.6 g (0.02 mole) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid are heated at 80° C. with 4.5 g of methyl 2-chloroacetoacetate and 4.2 g of triethylamine in 100 ml of dimethylformamide for 3 hours. The solution is then concentrated in vacuo, the residue is stirred with 50 ml of water and the resulting solid product is washed with water and methanol and recrystallised from glycol monomethyl ether. 3.9 g (44% of theory) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-{4-[2-oxo-1-(methoxycarbonyl)-1-propyl]-1-piperazinyl}-3-quinolinecarboxylic acid of decomposition point 224° to 228° C. are isolated.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04559342 |
| Source dataset | uspto-grants-1985_12 |
| ORD ID | ord-76c8c0f554984a2f93353489a4833afa |
| Source note | uspto-grants-1985_12 |