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

HRID 735269Notes

Reaction equation

HRID 735269 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH3:23])[C:19](=[O:20])[C:18]3[C:13](=[CH:14][C:15](Cl)=[CH:16][CH:17]=3)[NH:12][C:11]2=[O:22])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>>[CH3:23][C:10]1([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[C:19](=[O:20])[C:18]2[C:13](=[CH:14][C:15]([N:28]3[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]3)=[CH:16][CH:17]=2)[NH:12][C:11]1=[O:22]

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 116169013-(4-nitro-phenyl)-7-chloro-3-methyl-1H-quinoline-2,4-dione

Product 1

HCID 116897353-methyl-7-(4-methyl-piperazine-1-yl)-3-(4-nitro-phenyl)-1H-quinoline-2,4-dioneYield 31%

Procedure

A mixture of 3-(4-nitro-phenyl)-7-chloro-3-methyl-1H-quinoline-2,4-dione (0.3 g, 0.90 mmol) and 1-methylpiperazine (3.0 mL) was heated at reflux temperature overnight. Excessive 1-methylpiperazine was removed by evaporation in vacuo. The residue was diluted with water (50 mL), and the resulting suspension was extracted with ethyl acetate (50 mL×3). The organic layer was washed with brine (50 ml×2), dried over anhydrous MgSO4, and concentrated under reduced pressure. The pure objective compound (0.11 g, 31%) 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), 2.35 (s, 3H, NCH3), 2.50-2.55 (m, 4H, NCH2), 3.35-3.44 (m, 4H, NCH2), 6.13 (d, J=2.4 Hz, 1H, ArH), 6.64 (dd, J=9.2, 2.4 Hz, 1H, ArH), 7.52 (d, J=9.0 Hz, 2H, ArH), 7.82 (d, J=8.8 Hz, 1H, ArH), 8.15 (d, J=9.2 Hz, 2H, ArH); m.p. 150-151° C.; MS(EI) m/e 394 [M+].

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature overnight
  3. customExcessive 1-methylpiperazine was removed by evaporation in vacuo
  4. additionThe residue was diluted with water (50 mL)
  5. extractionthe resulting suspension was extracted with ethyl acetate (50 mL×3)
  6. washThe organic layer was washed with brine (50 ml×2)
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-118feb0e44454802ba0d6fc817808e5b
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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