Réaction #346908

Équation de réaction

ethyl 4-cyano-6,7-dihydro-1,3-dimethyl-1H-indazole-5-carboxylate

o-chloranil

→

title product

Rendement 47.3%

Ethyl 4-cyano-1,3-dimethyl-1H-indazole-5-carboxylate

Rendement 47.3%

Solvants

benzene

Conditions de réaction

Traitement

1. 1
   Températureat reflux temperature
2. 2
   Températurecooled
3. 3
   Filtrationfiltered
4. 4
   ConcentrationThe filtrate is concentrated in vacuo
5. 5
   Filtrationfiltered through two pads of neutral alumina
6. 6
   Autreevaporated to dryness
7. 7
   Autreto afford a yellow solid
8. 8
   AutreRecrystallization from ethyl acetate

Mode opératoire

A mixture of ethyl 4-cyano-6,7-dihydro-1,3-dimethyl-1H-indazole-5-carboxylate (13.5 g, 55.0 mmol), o-chloranil (16.3 g, 66.0 mmol) and dry benzene is stirred for 1.5 hours at reflux temperature, cooled and filtered. The filtrate is concentrated in vacuo, filtered through two pads of neutral alumina and evaporated to dryness to afford a yellow solid. Recrystallization from ethyl acetate affords the title product (6.33 g, 47.2%), mp 170°-175.5° C.

Source