Chlorine → HCID 12733914, compound

HRID 1578257Notes

Reaction equation

HRID 1578257 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].[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.ClCl>COCCO.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:23]1[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]1)[N:8]([CH2:13][CH3:14])[CH:7]=[C:6]([C:15]([OH:17])=[O:16])[C:5]2=[O:18]

Participants

6

Reactant 3

HCID 24526ChlorineHCID 531671-MethylpiperazineHCID 12733886HCID 12733886, compound

Product 1

HCID 12733914HCID 12733914, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 80192-MethoxyethanolSolvent

Procedure

A solution of 4.3 g (0.015 mol) of 6,7-dichloro-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid and 9 g of 1-methylpiperazine in a mixture of methyl cellosolve (45 cm3) and dimethylformamide (10 cm3) was heated to reflux temperature. After 6 hours, 75% of the theoretical amount of ionized chlorine (1 atom) had been released into the mixture. Heating was continued for a further 2 hours. The solution was concentrated to dryness in vacuo. The residue was taken up in 20 cm3 of ethanol. The solid, which was filtered off and recrystallised from methyl cellosolve, gave 2.78 g of 6-chloro-1-ethyl-7-(4-methylpiperazinyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, m.p. 260° C., which was identical to the compound described in Example 1.

Workup

  1. temperaturewas heated
  2. temperatureto reflux temperature
  3. temperatureHeating
  4. waitwas continued for a further 2 hours
  5. concentrationThe solution was concentrated to dryness in vacuo
  6. filtrationThe solid, which was filtered off
  7. customrecrystallised from methyl cellosolve

Sources & evidence

ORD record
ord-f389cab282ec4b5da1a5ce97f6951e82
Source dataset
uspto-grants-1981_09
Patent number
US04292317

Reaction notes

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