ethyl 2-(5-nitro-1H-indol-2-yl)propanoate → ethyl 2-(5-amino-1H-indol-2-yl)propanoate

HRID 468432노트

반응식

HRID 468432 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7]2)([O-])=O.O.O.[Sn](Cl)(Cl)(Cl)Cl>C(O)C.C(OCC)(=O)C.O.C([O-])(O)=O.[Na+]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7]2

참가 물질

7

반응물 2

HCID 59129193ethyl 2-(5-nitro-1H-indol-2-yl)propanoateHCID 85782573Tin tetrachloride dihydrate

생성물 1

HCID 59129453ethyl 2-(5-amino-1H-indol-2-yl)propanoate수율 99.7%

시약·촉매·용매 4

HCID 702Ethanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
120 °C

실험 절차

To a solution of ethyl 2-(5-nitro-1H-indol-2-yl)propanoate (0.10 g, 0.38 mmol) in ethanol (4 mL) was added tin chloride dihydrate (0.431 g, 1.91 mmol). The mixture was heated in the microwave at 120° C. for 1 h. The mixture was diluted with ethyl acetate before water and saturated aqueous NaHCO3 were added. The reaction mixture was filtered through a plug of celite using ethyl acetate. The organic layer was separated from the aqueous layer. The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure to give ethyl 2-(5-amino-1H-indol-2-yl)propanoate (0.088 g, 99%).

후처리

  1. additionwere added
  2. filtrationThe reaction mixture was filtered through a plug of celite
  3. customThe organic layer was separated from the aqueous layer
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-33db963813cb415e92205dc8bf4b21c5
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623905B2

반응 노트

불러오는 중…