Reacción #89790

Ecuación de reacción

3-hydrazinobenzoic acid

isopropylmethylketone

→

product

Rendimiento 81.4%

2,3,3-Trimethyl-4-carboxy-3H-indole

Rendimiento 81.4%

Disolventes

ethanol

sulfuric acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaunder reflux in an oil bath for 20 h
2. 2
   Otrowas evaporated off under reduced pressure to a small volume of ˜200 mL
3. 3
   OtroCollected the solid with a filter funnel
4. 4
   Lavadowashed with iPrOH (3×30 mL) and ethyl ether (3×30 mL)
5. 5
   Otrodried
6. 6
   OtroFurther drying of the solid in an oven at 45° C. under high vacuum for 18 h

Procedimiento

A solution of 3-hydrazinobenzoic acid (30.0 g, 197 mmol), isopropylmethylketone (31.7 mL, 296 mmol) in ethanol (500 mL) and sulfuric acid (5 mL) was heated under reflux in an oil bath for 20 h. After cooling to ambient temperature the solvent was evaporated off under reduced pressure to a small volume of ˜200 mL. Collected the solid with a filter funnel, washed with iPrOH (3×30 mL) and ethyl ether (3×30 mL) and dried. Further drying of the solid in an oven at 45° C. under high vacuum for 18 h provided 32.59 g (81.3%) of the product.

Fuente