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Acetone → Ethyl(E)-3-[2-amino-4-(4-nitrophenoxy)-3-pyridyl]-2-propenoate

HRID 387795
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HRID 387795 반응식
I[C:2]1[C:3]([NH2:18])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.[C:19]([O:23][CH2:24][CH3:25])(=[O:22])[CH:20]=[CH2:21].C(N(CCCC)CCCC)CCC.CC(C)=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[NH2:18][C:3]1[C:2](/[CH:21]=[CH:20]/[C:19]([O:23][CH2:24][CH3:25])=[O:22])=[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 180AcetoneHCID 7622TributylamineHCID 8821Ethyl AcrylateHCID 229363343-Iodo-4-(4-nitrophenoxy)-2-pyridinamine

생성물 1

HCID 58931221Ethyl(E)-3-[2-amino-4-(4-nitrophenoxy)-3-pyridyl]-2-propenoate

시약·촉매·용매 2

HCID 167845palladium(II) acetate
촉매
HCID 962Water용매

실험 절차

3-Iodo-4-(4-nitrophenoxy)-2-pyridineamine (500 mg), ethyl acrylate (0.3 ml), palladium (II) acetate (30 mg), tributylamine (0.66 ml) and dimethylformaldehyde (5 ml) were stirred at 130° C. for 20 minutes. After returning the reaction solution to room temperature, water was added and extraction was performed with ethyl acetate. NH type silica gel was added to the extract, the solvent was distilled off under reduced pressure, and the reaction product was adsorbed onto the silica gel. The silica gel was charged into a dry column packed with NH type silica gel, and column purification was performed (hexane:ethyl acetate=3:1). The solvent was distilled off under reduced pressure to obtain 330 mg of the target substance as a yellow oil.

후처리

  1. customto room temperature
  2. extractionextraction
  3. additionNH type silica gel was added to the extract
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionThe silica gel was charged into a dry column
  6. custompacked with NH type silica gel, and column purification
  7. distillationThe solvent was distilled off under reduced pressure
  8. customto obtain 330 mg of the target substance as a yellow oil

출처 및 근거

ORD 기록
ord-f92ef3996e974631b8f8793a5b7f8d77
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08372981B2

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