Reacción #699586

Ecuación de reacción

3-methoxy-1-(3-methoxyphenyl)-2-oxo-4-propionyl-1,2,5,6-tetrahydro-pyridine

cyclopentylhydrazine hydrochloride

sodium methoxide

→

1-cyclopentyl-3-ethyl-6(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1-H-pyrazolo[3,4-c]pyridine

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated to reflux
2. 2
   Concentraciónthe mixture was concentrated under reduced pressure
3. 3
   Otrochromatographed on a silica gel column
4. 4
   Otroto give a white solid
5. 5
   OtroRecrystallization from ether
6. 6
   Otrogave white needles

Procedimiento

A stirred mixture of 3-methoxy-1-(3-methoxyphenyl)-2-oxo-4-propionyl-1,2,5,6-tetrahydro-pyridine (0.49 grams, 1.7 mmole), cyclopentylhydrazine hydrochloride (0.40 grams) and sodium methoxide (46 mg, 0.85 mmole) in anhydrous ethanol was heated to reflux. After 16 hours, the mixture was concentrated under reduced pressure and chromatographed on a silica gel column using 1:4 ethyl acetate/hexane as eluent to give a white solid. Recrystallization from ether gave white needles. M.P. 64.65° C.; MS m/z [M+] 340.2025; HRMS [M+] 340.2046.

Fuente