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

HRID 1034558
Notes
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Reaction equation

HRID 1034558 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962
Water
Solvent

Conditions

Temperature
110 °C

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-aeec9057008e49d596a500e417dd3173
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08546049B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes