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

HRID 735267Notes

Reaction equation

HRID 735267 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:22])[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13](Cl)=[CH:14][C:15]=3[Cl:19])[NH:10][C:9]2=[O:21])=[CH:4][CH:3]=1.[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>N1C=CC=CC=1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:22])[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13]([N:27]4[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]4)=[CH:14][C:15]=3[Cl:19])[NH:10][C:9]2=[O:21])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 115735593-(4-amino-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dione

Product 1

HCID 116756863-(4-amino-phenyl)-5-chloro-3-methyl-7-(4-methyl-piperazine-1-yl)-1H-quinoline-2,4-dioneYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-(4-amino-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dione (0.1 g, 0.30 mmol) and 1-methylpiperazine (36 mL, 0.36 mmol) in dry pyridine (5.0 mL) was heated at reflux temperature overnight. After evaporation of the solvent in vacuo, the residue was diluted with water (50 mL), and resulting suspension was extracted with ethyl acetate (50 mL×3). The organic layer was washed with brine (50 mL×2) and dried over anhydrous MgSO4 concentrated under reduced pressure. The pure objective compound (87 mg, 73%) was obtained as yellow solid by a flash column chromatography (CH2Cl2:MeOH=20:1): 1H NMR (200 MHz, CDCl3) δ 1.78 (s, 3H, CH3) 2.35 (s, 3H, NCH3), 2.43-2.67 (m, 4H, NCH2), 2.90-2.95 (m, 4H, NCH2), 3.67 (br s, 2H, NH2), 6.38 (d, J=1.8 Hz, 1H, ArH), 6.54-6.61 (m, 3H, ArH), 7.04 (d, J=8.6 Hz, 2H, ArH), 8.44 (br s, 1H, NH).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature overnight
  3. customAfter evaporation of the solvent in vacuo
  4. additionthe residue was diluted with water (50 mL)
  5. customresulting suspension
  6. extractionwas extracted with ethyl acetate (50 mL×3)
  7. washThe organic layer was washed with brine (50 mL×2)
  8. dry with materialdried over anhydrous MgSO4
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8a7abe58abc949ffa79e4f14d7df4361
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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