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

HRID 1034558
ノート
印刷プレビュー

反応式

HRID 1034558 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

反応条件

温度
110 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-aeec9057008e49d596a500e417dd3173
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08546049B2

反応ノート

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