Methyl 3-(2-nitrophenyl)prop-2-enoate → Methyl 2-aminocinnamate

HRID 1919553

반응식

HRID 1919553 반응식
[N+:1]([C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[O:9])([O-])=O.Cl[Sn]Cl.O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:1][C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[O:9]

참가 물질

5

반응물 3

HCID 220809Methyl 3-(2-nitrophenyl)prop-2-enoateHCID 516892Sodium BicarbonateHCID 43835034Tin dichloride dihydrate

생성물 1

HCID 53439609Methyl 2-aminocinnamate수율 90.1%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

To a solution of methyl 2-nitrocinnamate (8) (11.03 g, 53.24 mmol) in ethyl acetate (200 ml) was added SnCl2.H2O (60.06 g, 266.19 mmol) at room temperature, and the resulting solution was stirred at 70° C. for 60 minutes. After the reaction was completed, the solution was allowed to cool to room temperature, basified with a saturated aqueous solution of sodium bicarbonate to weak basicity, and filtered with celite. The aqueous phase was extracted with ethyl acetate three times, and the combined organic phase was dried with anhydrous magnesium sulfate and distilled under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent: ethyl acetate:hexane=1:5) to give the target compound (8.50 g, 90%).

후처리

  1. temperatureto cool to room temperature
  2. filtrationfiltered with celite
  3. extractionThe aqueous phase was extracted with ethyl acetate three times
  4. dry with materialthe combined organic phase was dried with anhydrous magnesium sulfate
  5. distillationdistilled under reduced pressure

출처 및 근거

ORD 기록
ord-c952aeb9b48f4580a35321df13a1dbe6
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168646B2

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