Hydrochloric Acid → HCID 12944905, compound

HRID 1578269Notes

Reaction equation

HRID 1578269 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1Cl)[N:8]([CH3:13])[CH:7]=[C:6]([C:14]([OH:16])=[O:15])[C:5]2=[O:17].[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[N:8]([CH3:13])[CH:7]=[C:6]([C:14]([OH:16])=[O:15])[C:5]2=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4837PiperazineHCID 54183884HCID 54183884, compound

Product 1

HCID 12944905HCID 12944905, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.45 g of 6,7-dichloro-1-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, 3.1 g of piperazine and 30 cm3 of pyridine were heated under reflux for 8 hours. The dihalogeno-acid went rapidly into solution; after 5 hours, a precipitate appeared which consisted principally of the hydrochloride of the reaction product. The solvent was evaporated off, the residue was taken up in 100 cm3 of water, and 20 cm3 of N sodium hyxroxide solution were then added to the mixture. The solution, which was slightly turbid, was brought to pH 7.5, by the addition of acetic acid. The precipitate was filtered off and suspended in 100 cm3 of water; the addition of 10 cm3 of N HCl led to almost total dissolution. A slight amount of insoluble material was removed by filtration. The solution was brought to pH 7.5 by the addition of N NaOH. The solid was filtered off and recrystallised from a mixture of DMF (1 volume) and methyl cellosolve (2 volumes). 1.32 g of 6-chloro-1-methyl-4-oxo-7-piperazinyl-1,4-dihydro-quinoline-3-carboxylic acid, m.p. 288° C., were obtained.

Workup

  1. temperatureunder reflux for 8 hours
  2. customThe solvent was evaporated off
  3. addition20 cm3 of N sodium hyxroxide solution were then added to the mixture
  4. additionwas brought to pH 7.5, by the addition of acetic acid
  5. filtrationThe precipitate was filtered off
  6. additionthe addition of 10 cm3 of N HCl
  7. dissolutionled to almost total dissolution
  8. customA slight amount of insoluble material was removed by filtration
  9. additionThe solution was brought to pH 7.5 by the addition of N NaOH
  10. filtrationThe solid was filtered off
  11. customrecrystallised from a mixture of DMF (1 volume) and methyl cellosolve (2 volumes)

Sources & evidence

ORD record
ord-6025b59e1d614994855bf43ef5cd94fe
Source dataset
uspto-grants-1981_09
Patent number
US04292317

Reaction notes

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