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 735245ノート

反応式

HRID 735245 の反応式
[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

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-f40866b9d98a41c182501e72caf17905
出典データセット
uspto-grants-2009_09
特許番号
US07592457B2

反応ノート

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