Potassium Carbonate → 2-(2,4-Dimethoxybenzylamino)-4-methylaniline

HRID 857873

반응식

HRID 857873 반응식
[CH3:1][O:2][C:3]1[C:10](OC)=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].[C:13](=[O:16])([O-])[O-].[K+].[K+].F[C:20]1[CH:21]=[C:22]([CH3:29])[CH:23]=[CH:24][C:25]=1[N+:26]([O-])=O.[Cl-].[NH4+]>CN1CCCC1=O.C(O)C.[Fe].O.CCOCC>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:16][CH3:13])[CH:8]=[CH:7][C:4]=1[CH2:5][NH:6][C:20]1[CH:21]=[C:22]([CH3:29])[CH:23]=[CH:24][C:25]=1[NH2:26]

참가 물질

10

반응물 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 781062,3-Dimethoxybenzylamine

생성물 1

HCID 223857232-(2,4-Dimethoxybenzylamino)-4-methylaniline수율 67.1%

시약·촉매·용매 5

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
120 °C

실험 절차

2,3-Dimethoxybenzylamine (1.05 g) and potassium-carbonate (1.52 g) were added to a solution of 3-fluoro-4-nitrotoluene (0.832 g) in 1-methyl-2-pyrrolidinone (5.0 ml), and the mixture was stirred at 120° C. for 4 hours. Then, ether was added to the reaction mixture. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo to give a yellow oil. The yellow oil was dissolved in ethanol (100 ml), and to the solution were added water (50 ml), saturated aqueous ammonium chloride (50 ml) and iron dust (352 g). The mixture was heated under reflux for 3 hours while vigorous stirring. Then insolubles were removed by filtration, and the filtrate was concentrated in vacuo. The residue was dissolved in chloroform, and the organic layer was washed with water and brine and dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate, 3:1 to 2:1) and then recrystallized by ethyl acetate-hexane to give the title compound (0.980 g).

후처리

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give a yellow oil
  6. temperatureThe mixture was heated
  7. temperatureunder reflux for 3 hours while vigorous stirring
  8. customThen insolubles were removed by filtration
  9. concentrationthe filtrate was concentrated in vacuo
  10. dissolutionThe residue was dissolved in chloroform
  11. washthe organic layer was washed with water and brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. filtrationfiltered
  14. concentrationThe filtrate was concentrated in vacuo
  15. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate, 3:1 to 2:1)
  16. customrecrystallized by ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-3e441a221e094f7184f773fbdac704c8
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148224B2

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