Chlorine → HCID 12944901, compound

HRID 1578265Notes

Reaction equation

HRID 1578265 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].[CH2:19]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[CH:20]=[CH2:21].ClCl>N1C=CC=CC=1>[CH2:19]([N:22]1[CH2:27][CH2:26][N:25]([C:11]2[CH:10]=[C:9]3[C:4]([C:5](=[O:18])[C:6]([C:15]([OH:17])=[O:16])=[CH:7][N:8]3[CH2:13][CH3:14])=[CH:3][C:2]=2[Cl:1])[CH2:24][CH2:23]1)[CH:20]=[CH2:21]

Participants

5

Reactant 3

HCID 24526ChlorineHCID 8064221-AllylpiperazineHCID 12733886HCID 12733886, compound

Product 1

HCID 12944901HCID 12944901, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2 g of 6,7-dichloro-1-ethyl-4-oxo-1,4-dihydro quinoline-3-carboxylic acid, 3.8 g of 1-allylpiperazine and 20 cm3 of pyridine were heated under reflux. After 2 hours, dissolution of the acid was complete; after 11 hours, determination of the ionised chlorine (93% of theory) showed that the reaction was substantially complete. The solution was concentrated to dryness in vacuo, the residue was taken up in water (20 cm3) and the suspension was brought to pH 7.5 by the addition of acetic acid, whilst stirring. The precipitate was filtered off, washed with water and recrystallised from methyl cellosolve. 2.05 g of 7-(4-allylpiperazinyl)-6-chloro-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, m.p. 212° C., were obtained.

Workup

  1. temperatureunder reflux
  2. dissolutiondissolution of the acid
  3. waitafter 11 hours
  4. concentrationThe solution was concentrated to dryness in vacuo
  5. additionthe suspension was brought to pH 7.5 by the addition of acetic acid
  6. filtrationThe precipitate was filtered off
  7. washwashed with water
  8. customrecrystallised from methyl cellosolve

Sources & evidence

ORD record
ord-4037cfe8ba174cc4ba0625983bb698ec
Source dataset
uspto-grants-1981_09
Patent number
US04292317

Reaction notes

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