Pyridine → HCID 12944902, compound

HRID 1578266Notes

Reaction equation

HRID 1578266 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1Cl)[N:8]([CH2:13][CH3:14])[CH:7]=[C:6]([C:15]([OH:17])=[O:16])[C:5]2=[O:18].[C:19]1([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.N1C=CC=CC=1>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:28]1[CH2:29][CH2:30][N:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:26][CH2:27]1)[N:8]([CH2:13][CH3:14])[CH:7]=[C:6]([C:15]([OH:17])=[O:16])[C:5]2=[O:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 70961-PhenylpiperazineHCID 12733886HCID 12733886, compound

Product 1

HCID 12944902HCID 12944902, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.15 g of 6,7-dichloro-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, 6.5 g of 1-phenylpiperazine and 20 cm3 of pyridine were heated under reflux for 16 hours. The solvent was removed in vacuo and the residue was taken up in 20 cm3 of water. The suspension obtained was stirred and brought to pH 7 by the addition of acetic acid. The solid was filtered off and recrystallised from methyl cellosolve. 1.7 g of 6-chloro-1-ethyl-4-oxo-7-(4-phenylpiperazinyl)-1,4-dihydro-quinoline-3-carboxylic acid, m.p. 234°-235° C., were obtained.

Workup

  1. temperatureunder reflux for 16 hours
  2. customThe solvent was removed in vacuo
  3. customThe suspension obtained
  4. filtrationThe solid was filtered off
  5. customrecrystallised from methyl cellosolve

Sources & evidence

ORD record
ord-9fb47b30be1144629b35bdc98ebc312d
Source dataset
uspto-grants-1981_09
Patent number
US04292317

Reaction notes

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