1-Methylpiperazine → 5-chloro-3-methyl-7-(4-methyl-piperazine-1-yl)-3-(4-nitro-phenyl)-1H-quinoline-2,4-dione

HRID 735268Notes

Reaction equation

HRID 735268 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH3:24])[C:19](=[O:20])[C:18]3[C:13](=[CH:14][C:15](Cl)=[CH:16][C:17]=3[Cl:21])[NH:12][C:11]2=[O:23])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>N1C=CC=CC=1>[Cl:21][C:17]1[CH:16]=[C:15]([N:29]2[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]2)[CH:14]=[C:13]2[C:18]=1[C:19](=[O:20])[C:10]([CH3:24])([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[C:11](=[O:23])[NH:12]2

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 115667753-(4-nitro-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dione

Product 1

HCID 115464395-chloro-3-methyl-7-(4-methyl-piperazine-1-yl)-3-(4-nitro-phenyl)-1H-quinoline-2,4-dioneYield 46%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-(4-nitro-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dione (0.3 g, 0.82 mmol) and 1-methylpiperazine (123 mL, 1.23 mmol) in dry pyridine (5.0 mL) was heated at reflux temperature for 5 hours. After evaporation of the solvent in vacuo, the residue was diluted with water (100 mL), and the resulting suspension was extracted with ethyl acetate (100 mL×3). The organic layer was washed with brine (100 mL×2), dried over anhydrous MgSO4 concentrated under reduced pressure. The pure objective compound (0.16 g, 46%) was obtained as yellow solid by a flash column chromatography (CH2Cl2:MeOH=20:1): 1H NMR (200 MHz, CDCl3) δ 1.90 (s, 3H, CH3), 2.34 (s, 3H, NCH3), 2.54-2.59 (m, 4H, NCH2), 2.88-3.07 (m, 4H, NCH2), 6.43 (d, J=1.8 Hz, 1H, ArH), 6.64 (d, J=2.0 Hz, 1H, ArH), 7.46 (d, J=9.0 Hz, 2H, ArH), 8.17 (d, J=9.0 Hz, 2H, ArH), 8.64 (br s, 1H, NH).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 5 hours
  3. customAfter evaporation of the solvent in vacuo
  4. additionthe residue was diluted with water (100 mL)
  5. extractionthe resulting suspension was extracted with ethyl acetate (100 mL×3)
  6. washThe organic layer was washed with brine (100 mL×2)
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b3b4e68c8f31450791264d3e49bdf6a3
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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