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

HRID 1909008노트

반응식

HRID 1909008 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 203767455-(2-Dimethylamino-ethoxy)-2-nitro-phenylamine수율 90%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
0 °C

실험 절차

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)+

후처리

  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)

출처 및 근거

ORD 기록
ord-a30b3142357e4b5ab783a177a277fad8
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598217B2

반응 노트

불러오는 중…