Réaction #699586

Équation de réaction

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

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   Températurewas heated to reflux
2. 2
   Concentrationthe mixture was concentrated under reduced pressure
3. 3
   Autrechromatographed on a silica gel column
4. 4
   Autreto give a white solid
5. 5
   AutreRecrystallization from ether
6. 6
   Autregave white needles

Mode opératoire

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.

Source