Potassium Carbonate → 1,8-Naphthyridine-3-carboxylic acid, 1,4-dihydro-6-chloro-1-ethenyl-4-oxo-7-(1-piperazinyl)-

HRID 223154Notes

Reaction equation

HRID 223154 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[N:25]=[C:24]3[C:19]([C:20](=[O:34])[C:21]([C:29]([O:31]CC)=[O:30])=[CH:22][N:23]3[CH2:26][CH2:27]Cl)=[CH:18][C:17]=2[Cl:35])[CH2:12][CH2:11]1)(=O)C>C(O)C.Cl.O.N>[Cl:35][C:17]1[CH:18]=[C:19]2[C:24](=[N:25][C:16]=1[N:13]1[CH2:14][CH2:15][NH:10][CH2:11][CH2:12]1)[N:23]([CH:26]=[CH2:27])[CH:22]=[C:21]([C:29]([OH:31])=[O:30])[C:20]2=[O:34]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 20519047HCID 20519047, compound

Product 1

HCID 30583801,8-Naphthyridine-3-carboxylic acid, 1,4-dihydro-6-chloro-1-ethenyl-4-oxo-7-(1-piperazinyl)-Yield 51.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 12896473Azane;hydrateSolvent

Procedure

To a solution of potassium carbonate (1.52 g) in ethanol (40 ml) which was kept at 90°-95° C., was added ethyl 7-(4-acetyl-1-piperazinyl)-6-chloro-1-(2-chloroethyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (4.0 g) and the mixture was heated to reflux for 1.5 hours. After the mixture was cooled, the resulting potassium 7-(4-acetyl-1-piperazinyl)-6-chloro-1,4-dihydro-4-oxo-1-vinyl-1,8-naphthyridine-3-carboxylate was collected, and dissolved in 30 ml of water and 20 ml of 1 N sodium hydroxide. The mixture was heated to reflux for 2 hours and acidified with acetic acid, and then adjusted to pH 8 with ammonia solution to give a precipitate. The precipitate was dissolved in diluted hydrochloric acid and adjusted again to pH 8 with ammonia water to give 1.56 g of 6-chloro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1-vinyl-1,8-naphthyridine-3-carboxylic acid, m.p. 272°-274° C.

Workup

  1. customwas kept at 90°-95° C.
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 1.5 hours
  4. temperatureAfter the mixture was cooled
  5. customthe resulting potassium 7-(4-acetyl-1-piperazinyl)-6-chloro-1,4-dihydro-4-oxo-1-vinyl-1,8-naphthyridine-3-carboxylate was collected
  6. dissolutiondissolved in 30 ml of water
  7. temperatureThe mixture was heated
  8. temperatureto reflux for 2 hours
  9. customto give a precipitate

Sources & evidence

ORD record
ord-772d87dec6c04a19bae6deeebe166cf2
Source dataset
uspto-grants-1982_10
Patent number
US04352803

Reaction notes

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