Reacción #63487

Ecuación de reacción

ammonia

nitric acid

3-(2,3-dihydro-6-methyl-8α-ergolinyl)-1,1-diethylurea

→

3-(2,3-dihydro-6-methyl-13-nitro-8α-ergolinyl)-1,1-diethylurea

Rendimiento 71.0%

Disolventes

sulfuric acid

sulfuric acid

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThe reaction solution is then slowly introduced dropwise into ice
2. 2
   Extracciónextracted
3. 3
   workup.STIRRINGby shaking with methylene chloride
4. 4
   LavadoAfter washing the organic phase with water
5. 5
   Secadodrying with magnesium sulfate
6. 6
   Otrothe nitrated compound is obtained in a 90% crude yield
7. 7
   OtroAfter chromatographic separation and purification

Procedimiento

Under ice cooling, 10 mmol of 3-(2,3-dihydro-6-methyl-8α-ergolinyl)-1,1-diethylurea is dissolved in 100 ml of concentrated sulfuric acid; 7 ml of a solution of 10 ml of 65% nitric acid in 90 ml of concentrated sulfuric acid is added thereto, and the mixture is stirred for 15 minutes in an ice bath. The reaction solution is then slowly introduced dropwise into ice, made alkaline under ice cooling with 32% ammonia solution, and extracted by shaking with methylene chloride. After washing the organic phase with water and drying with magnesium sulfate, the nitrated compound is obtained in a 90% crude yield. After chromatographic separation and purification, respectively, 3-(2,3-dihydro-6-methyl-13-nitro-8α-ergolinyl)-1,1-diethylurea is obtained in a 71% yield.

Fuente