2-(Dimethylamino)ethanol → 5-(2-Dimethylamino-ethoxy)-2-nitro-phenylamine

HRID 1909008ノート

反応式

HRID 1909008 の反応式
F[C:2]1[CH:3]=[C:4]([C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1)[NH2:5].[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][OH:16].[OH-].[K+]>C1(C)C=CC=CC=1.O>[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][O:16][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:4]([NH2:5])[CH:3]=1

参加物

6

反応物 3

HCID 79022-(Dimethylamino)ethanolHCID 14797Potassium HydroxideHCID 753995-Fluoro-2-nitroaniline

生成物 1

HCID 203767455-(2-Dimethylamino-ethoxy)-2-nitro-phenylamine収率 90%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

3-Fluoro-6-nitroaniline (0.7 g, 4.48 mmol) and N,N-dimethylethanolamine (1.34 mL, 13.45 mmol) were dissolved in toluene (5 mL). This solution was cooled at 0° C. and finely ground KOH (1.258 g, 22.4 mmol) was added to the stirring mixture. The reaction mixture was stirred for 16 hours at room temperature, diluted with H2O (30 mL) and then extracted with CHCl3 (3×25 mL). The combined organics were dried (Na2SO4), filtered and the solvent was removed in vacuo. Purification by SiO2 chromatography (0% to 10% 2.0M NH3 in MeOH/dichloromethane) gave 5-(2-dimethylamino-ethoxy)-2-nitro-phenylamine as a dark oil (0.665 g, 90%). MS(ESI) m/z 226.0 (M+H)+

後処理

  1. extractionextracted with CHCl3 (3×25 mL)
  2. dry with materialThe combined organics were dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. customPurification by SiO2 chromatography (0% to 10% 2.0M NH3 in MeOH/dichloromethane)

出典と根拠

ORDレコード
ord-a30b3142357e4b5ab783a177a277fad8
出典データセット
uspto-grants-2013_12
特許番号
US08598217B2

反応ノート

読み込み中…