3-(4-nitro-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dione → 3-(4-amino-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dione

HRID 735245Notes

Reaction equation

HRID 735245 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:24])[C:5]([CH3:23])([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=1)[C:6](=[O:13])[NH:7]2>CO>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([C:5]2([CH3:23])[C:4](=[O:24])[C:3]3[C:8](=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=3[Cl:1])[NH:7][C:6]2=[O:13])=[CH:19][CH:18]=1

Participants

3

Reactant 1

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

Product 1

HCID 115735593-(4-amino-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dioneYield 66.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5,7-dichloro-3-methyl-3-(4-nitro-phenyl)-1H-quinoline-2,4-dione (1.0 g, 2.74 mmol) in methanol (30 mL) was added SnCl2-2H2O (1.85 g, 8.22 mmol). The resulting solution was stirred at reflux temperature overnight. After the reaction was completed, a yellow residue was obtained after evaporating solvent under reduced pressure. The residue was then diluted with 1N HCl solution (200 mL), and extracted with ethyl acetate (200 mL×3). The combined organic layer was washed with brine (200 ml×2) and water (200 mL×2) and dried over magnesium sulfate anhydride. After evaporation of the solvent, the objective compound (0.61 g, 66%) was obtained as pale yellow solid by purifying the residue with flash column chromatography (n-hexane:ethyl acetate=4:1): 1H NMR (200 MHz, CDCl3) δ 1.68 (s, 3H, CH3), 3.68 (br s, 2H, NH2), 6.58 (d, J=8.8 Hz, 2H, ArH), 6.73 (d, J=1.8 Hz, 1H, ArH), 6.96 (d, J=8.8 Hz, 2H, ArH), 7.08 (d, J=1.8 Hz, 1H, ArH), 8.21 (br s, 1H, NH); MS(EI) m/e 335 [M++1].

Workup

  1. temperatureat reflux temperature overnight
  2. customa yellow residue was obtained
  3. customafter evaporating solvent under reduced pressure
  4. additionThe residue was then diluted with 1N HCl solution (200 mL)
  5. extractionextracted with ethyl acetate (200 mL×3)
  6. washThe combined organic layer was washed with brine (200 ml×2) and water (200 mL×2)
  7. dry with materialdried over magnesium sulfate anhydride
  8. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-f40866b9d98a41c182501e72caf17905
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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