Hydrochloric Acid → Nadifloxacin

HRID 434697Notes

Reaction equation

HRID 434697 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:17]([F:18])=[CH:16][CH:15]=[C:14]3[C:9]=2[CH2:10][CH2:11][C:12]([CH3:20])(C)[NH:13]3)[CH2:4][CH2:3]1.C([O:23][CH:24]=[C:25]([C:31](OCC)=O)[C:26]([O:28]CC)=[O:27])C.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.P(=O)(O)(O)O.[OH-].[Na+].Cl>>[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]2[C:9]3=[C:14]4[N:13]([CH:12]([CH3:20])[CH2:11][CH2:10]3)[CH:31]=[C:25]([C:26]([OH:28])=[O:27])[C:24](=[O:23])[C:15]4=[CH:16][C:17]=2[F:18])[CH2:6][CH2:7]1

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 1004Phosphoric AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 54153450HCID 54153450, compound

Product 1

HCID 4410NadifloxacinYield 5.1%

Conditions

Temperature
160 °C

Procedure

A mixture of 6.6 g of 5-(4-hydroxy-1-piperidyl)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinaldine and 6.0 g of diethyl ethoxymethylenemalonate was reacted by heating at 160° C. for 30 minutes. Then, 48 g of polyphosphoric acid prepared from 24 g of phosphorus pentoxide and 24 g of phosphoric acid was added thereto and the resulting mixture was reacted by heating at 150°-160° C. for 1 hour. After completion of the reaction the reaction mixture was poured into 150 g of ice water. Precipitations which formed were collected by filtration, washed with water and dried. To the crystals thus obtained were added 70 ml of a 10% aqueous sodium hydroxide solution and the mixture was reacted at 100°-110° C. for 1 hour. After cooling, the reaction mixture was rendered acidic with concentrated hydrochloric acid to precipitate crystals, which then were collected by filtration, washed with water and recrystallized from ethanol-water to give 440 mg of 8-(4-hydroxy-1-piperidyl)-9-fluoro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid. m.p. 244°-247° C.

Workup

  1. customwas reacted
  2. additionwas added
  3. customthe resulting mixture was reacted
  4. temperatureby heating at 150°-160° C. for 1 hour
  5. customAfter completion of the reaction the reaction mixture
  6. customPrecipitations which
  7. customformed
  8. filtrationwere collected by filtration
  9. washwashed with water
  10. customdried
  11. customTo the crystals thus obtained
  12. customthe mixture was reacted at 100°-110° C. for 1 hour
  13. temperatureAfter cooling
  14. customto precipitate crystals, which
  15. filtrationthen were collected by filtration
  16. washwashed with water
  17. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-42dfdf3600114c53add082b03dfc4db5
Source dataset
uspto-grants-1983_08
Patent number
US04399134

Reaction notes

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