Sodium Hydroxide → 5-[1-(3,5-Dimethoxy-phenyl)-propenyl]-2-methoxy-phenylamine

HRID 2378266ノート

反応式

HRID 2378266 の反応式
O.O.Cl[Sn]Cl.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([N+:27]([O-])=O)[CH:20]=2)=[CH:17][CH3:18])[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1.[OH-].[Na+]>C(O)C.C(OCC)(=O)C>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([NH2:27])[CH:20]=2)=[CH:17][CH3:18])[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 692040644-[1-(3,5-Dimethoxy-phenyl)-propenyl]-1-methoxy-2-nitro-benzene

生成物 1

HCID 692036045-[1-(3,5-Dimethoxy-phenyl)-propenyl]-2-methoxy-phenylamine収率 66.8%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

SnCl2.2H2O (5.20 g, 23.0 mmol) was added to a stirred solution of (E/Z) 4-[1-(3,5-dimethoxy-phenyl)-propenyl]-1-methoxy-2-nitro-benzene (1.10 g, 3.2 mmol) in ethanol (200 proof, 20 mL) and ethyl acetate (10 mL). The reaction mixture was heated at 70° C. for 1 h. The solution was cooled down to room temperature, poured into ice water (100 mL), and basified with 10 N NaOH (20 mL) to pH ˜12. The aqueous layer was extracted with ethyl acetate (5×35 mL). The combined organic layers were washed with water (60 mL), brine (50 mL) and dried (MgSO4). Removal of solvent and chromatography (Silica Gel) gave a mixture of (E/Z) 5-[1-(3,5-dimethoxy-phenyl)-propenyl]-2-methoxy-phenylamine as an oil (0.64 g, 51% yield): 1H NMR (CDCl3) δ 1.70-1.78 (2d, J=7.0 Hz, 6H, 2CH3), 3.74-3.87 (4s+m, 22H, 6OCH3+2NH2), 6.02-6.10 (m, 2H, 2CH), 6.33-6.79 (m, 12H, Ar); 13C NMR (CDCl3) δ 15.60, 15.73, 55.30, 55.45, 55.52, 98.70, 98.92, 105.72, 107.99, 109.95, 109.99, 113.91, 116.77, 117.30, 120.32, 122.05, 123.83, 132.49, 135.56, 135.61, 142.09, 142.33, 142.50, 145.66, 146.32, 146.56, 160.36, 160.51; Anal. Calcd for C18H21NO3: C, 72.22; H, 7.07; N, 4.68. Found: C, 71.94; H, 7.37; N, 4.54.

後処理

  1. temperatureThe solution was cooled down to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate (5×35 mL)
  3. washThe combined organic layers were washed with water (60 mL), brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. customRemoval of solvent and chromatography (Silica Gel)
  6. customgave

出典と根拠

ORDレコード
ord-f74be3d125824eb18db6da8bb9946212
出典データセット
uspto-grants-2008_12
特許番号
US07470723B2

反応ノート

読み込み中…