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 735245노트

반응식

HRID 735245 반응식
[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

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-f40866b9d98a41c182501e72caf17905
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592457B2

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