Reaktion #46393

Reaktionsgleichung

HCl

3,3-dioxo-1,2,3,6-tetrahydro-3λ6-thieno[3,2-e]indole-7,8-dione

sodium hydroxide

hydrogen peroxide

→

desired compound

Ausbeute 60.6%

5-amino-1,1-dioxo-2,3-dihydro-1H-1λ6-benzo[b]thiophene-4-carboxylic acid

Ausbeute 60.6%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe internal temperature during the addition
2. 2
   Sonstigewas kept between 30-40° C. despite the exothermic reaction
3. 3
   workup.ADDITIONAfter the addition
4. 4
   TemperaturThe mixture was then cooled to RT
5. 5
   Filtrationthe precipitated solid was filtered off with suction
6. 6
   WaschenThe latter was washed successively with water and diethyl ether
7. 7
   Sonstigedried in vacuo overnight

Vorschrift

1.5 g (6.32 mmol) of 3,3-dioxo-1,2,3,6-tetrahydro-3λ6-thieno[3,2-e]indole-7,8-dione were introduced into a 10 ml three-neck round-bottom flask and dissolved in 6.5 ml of 1M (207.2 mmol) sodium hydroxide solution. 1.5 ml (1.32 mmol) of a 30% strength hydrogen peroxide solution were slowly added dropwise over the course of 30 minutes. The internal temperature during the addition was kept between 30-40° C. despite the exothermic reaction. After the addition was complete, the mixture was stirred at 40° C. for 1.5 h. The mixture was then cooled to RT and, after addition to a little water (about 7 ml), acidified with a 10% strength HCl to pH 1, and the precipitated solid was filtered off with suction. The latter was washed successively with water and diethyl ether and dried in vacuo overnight. 870 mg of the desired compound were obtained.

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