Methane → HCID 12944903, compound

HRID 1578267Notes

Reaction equation

HRID 1578267 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].[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:22]1[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]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 297MethaneHCID 531671-MethylpiperazineHCID 54183884HCID 54183884, compound

Product 1

HCID 12944903HCID 12944903, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.18 g of 6,7-dichloro-1-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, 3.5 cm3 of 1-methylpiperazine and 25 cm3 of dimethylsulphoxide were heated at 110° C. for 3 hours. The solvent was evaporated off in vacuo and the residue was taken up in 100 cm3 of water. The suspension was stirred and mixed with 20 cm3 of N sodium hydroxide solution. The solution obtained, which was slightly turbid, was stirred with animal charcoal and filtered, and then brought to pH 7.5 by the addition of acetic acid. The precipitate was filtered off, washed with water and then recrystallised from methyl cellosolve. 1 g of 6-chloro-1-methyl-7-(4-methylpiperazinyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, m.p. 286° C., were obtained.

Workup

  1. customThe solvent was evaporated off in vacuo
  2. additionmixed with 20 cm3 of N sodium hydroxide solution
  3. customThe solution obtained
  4. filtrationfiltered
  5. additionbrought 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-d60fbf235fd34354af2d9e36fb3e45e7
Source dataset
uspto-grants-1981_09
Patent number
US04292317

Reaction notes

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