Reaction #1121740

Reaction equation

1,4-dioxane

2-(p-nitrophenyl)-5-nitrobenzofurane

hydrochloric acid

→

2-(p-aminophenyl)-5-aminobenzofurane

Yield 90.0%

Solvents

water

—

mixed solvent

Conditions

Workup

1. 1
   Temperaturethe resulting mixture was refluxed
2. 2
   FiltrationThe hot supernatant was filtered with Celite immediately
3. 3
   Othera completion of the reaction by TLC (Thin-Layer Chromatography)
4. 4
   WashThe residual material was adequately washed with hot 1,4-dioxane
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated by an evaporator
7. 7
   ConcentrationAfter concentration, recrystallization

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%.

Source