3-(4-nitro-phenyl)-7-chloro-3-methyl-1H-quinoline-2,4-dione → HCID 11673838, compound

HRID 735263Notes

Reaction equation

HRID 735263 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:23])[C:7]([CH3:22])([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1>CO.Cl>[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([C:7]2([CH3:22])[C:6](=[O:23])[C:5]3[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=3)[NH:9][C:8]2=[O:12])=[CH:18][CH:17]=1

Participants

4

Reactant 1

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

Product 1

HCID 11673838HCID 11673838, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 7-chloro-3-methyl-3-(4-nitro-phenyl)-1H-quinoline-2,4-dione (0.98 g, 2.96 mmol) in methanol (10 mL) was added SnCl2-2H2O (2.0 g, 8.88 mmol). The resulting solution was stirred at reflux temperature overnight. After the reaction was completed, the solvent was evaporated under reduced pressure to produce pale yellow residue. The residue was diluted with 1N HCl solution (200 mL) and extracted with ethyl acetate (200 mL×3). The organic layer was washed with brine (200 ml×2) and water (200 ml×2) and dried over anhydrous MgSO4. After evaporation of the solvent, the objective compound (0.78 g, 88%) was obtained as pale yellow solid by purifying the residue with recrystallization (n-hexane:EtOAc=1:1): 1H NMR (200 MHz, CDCl3) δ 1.79 (s, 3H, CH3), 3.67 (br s, 2H, NH2), 6.57 (d, J=8.6 Hz, 2H, ArH), 6.92 (d, J=2.0 Hz, 1H, ArH), 7.03-7.09 (m, 3H, ArH), 7.83 (d, J=8.8 Hz, 1H, ArH), 9.01 (br s, 1H, NH); m.p. 155-156° C.; MS(EI) m/e 300 [M+].

Workup

  1. temperatureat reflux temperature overnight
  2. customthe solvent was evaporated under reduced pressure
  3. customto produce pale yellow residue
  4. extractionextracted with ethyl acetate (200 mL×3)
  5. washThe organic layer was washed with brine (200 ml×2) and water (200 ml×2)
  6. dry with materialdried over anhydrous MgSO4
  7. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-837515c86a714945b4a5f266aa0f008e
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

Loading…