Reacción #2267077

Ecuación de reacción

H3PO2

15

6-Amino-3-methyl-1-(4-nitrophenyl)-7-methoxyisochroman

NaNO2

→

desired product 16

Rendimiento 86.0%

3-Methyl-1-(4-nitrophenyl)-7-methoxyisochroman

Rendimiento 86.0%

Disolventes

H2SO4

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter refluxing for 5 hours
2. 2
   Extracciónthe solution was extracted with ethyl acetate three times
3. 3
   SecadoThe combined organic phases were dried over Na2SO4
4. 4
   OtroRemoval of the solvent
5. 5
   Otroafforded the crude product
6. 6
   OtroPurification of the crude product

Procedimiento

Solution of 15 (100 mg, 0.32 mmol) in 5 ml of 4N H2SO4 was treated with NaNO2 (29.6 mg, 1.16 eq) at 0° C. for 15 min, followed by adding H3PO2 (50%, 0.25 ml) at such temperature. After refluxing for 5 hours, the solution was extracted with ethyl acetate three times. The combined organic phases were dried over Na2SO4. Removal of the solvent afforded the crude product. Purification of the crude product by using silica gel column gave the desired product 16 (82 mg, 86%).

Fuente