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Hydrochloric Acid → 2-(4-Aminophenyl)-1-benzofuran-5-amine

HRID 1034558
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HRID 1034558 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:13]=3[CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.Cl.O1CCOCC1>[Fe].O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:13]=3[CH:14]=2)=[CH:6][CH:5]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 128136015-Nitro-2-(4-nitrophenyl)-1-benzofuran

생성물 1

HCID 111069902-(4-Aminophenyl)-1-benzofuran-5-amine수율 90%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

반응 조건

온도
110 °C

실험 절차

Then, 12.42 g (1.0 equivalent) of the obtained 2-(p-nitrophenyl)-5-nitrobenzofurane was added to 48.85 g (20.0 equivalents) of a 100 mesh iron powder previously activated by 0.5 ml of concentrated hydrochloric acid in 150 ml of a mixed solvent of 1,4-dioxane and water in proportions of 1:1, and the resulting mixture was refluxed by heating at about 110° C. for 2 hours and heavily stirred. The hot supernatant was filtered with Celite immediately after confirming a completion of the reaction by TLC (Thin-Layer Chromatography). The residual material was adequately washed with hot 1,4-dioxane and filtered. This operation was repeated three or four times, and then filtrates were combined and concentrated by an evaporator. After concentration, recrystallization was carried out with ethanol to obtain 7.1 g of orange-colored 2-(p-aminophenyl)-5-aminobenzofurane (amino compound A) at an yield of 90%.

후처리

  1. temperaturethe resulting mixture was refluxed
  2. filtrationThe hot supernatant was filtered with Celite immediately
  3. customa completion of the reaction by TLC (Thin-Layer Chromatography)
  4. washThe residual material was adequately washed with hot 1,4-dioxane
  5. filtrationfiltered
  6. concentrationconcentrated by an evaporator
  7. concentrationAfter concentration, recrystallization

출처 및 근거

ORD 기록
ord-aeec9057008e49d596a500e417dd3173
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08546049B2

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