3-Chloro-2-hydrazinylpyridine → Ethyl 1-(3-chloropyridin-2-yl)-5-hydroxy-3-(hydroxymethyl)-4,5-dihydro-1H-pyrazole-5-carboxylate
Reaktionsgleichung
CC1(C)O/[C:5](=[CH:7]/[C:8](=[O:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])/[CH2:4][O:3]1.[NH:16]([C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][N:19]=1)[NH2:17]>C(O)C>[Cl:24][C:23]1[C:18]([N:16]2[C:8]([OH:14])([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:7][C:5]([CH2:4][OH:3])=[N:17]2)=[N:19][CH:20]=[CH:21][CH:22]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
The mixture of ethyl (3E)-3-(2,2-dimethyl-1,3-dioxolan-4-ylidene)-2-oxopropanoate (21.4 g, 0.1 mol) and 2-hydrazino-3-chloropyridine (21.4 g, 0.15 mol) in 150 ml of ethanol was stirred for 8 hours at RT. Ethanol was removed in vacuo and the residue was taken up in 200 ml of methyl tert-butyl ethyl. The organic phase was washed three times with in each case 50 ml of 1% HCl and concentrated by evaporation. This gave 36 g (86% yield) of the product as a viscous oil with a purity (HPLC) of 97%.