Hydrazine hydrate (1:1) → 5-[4-(3-Amino-propoxy)-phenyl]-6-methyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile
Reaktionsgleichung
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[C:18]([C:24]#[N:25])[C:19](=[O:23])[NH:20][C:21]=3[CH3:22])=[CH:12][CH:11]=2)C(=O)C2=CC=CC=C12.O.NN>C(O)C>[NH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:17]=[C:18]([C:24]#[N:25])[C:19](=[O:23])[NH:20][C:21]=2[CH3:22])=[CH:14][CH:15]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 1.885 g (4.70 mmol) of 5-(4-phthalimidopropyloxyphenyl)-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile and 251 μl (5.17 mmol) of hydrazine monohydrate in 50 ml of ethanol is heated 16 hr at reflux. The volatiles are removed under vacuum and the residue is taken up in 15 ml of 1:1 CHCl3 :CH3 and flashchromatographed through a 6 inch length column of silica gel (90:10:2 CHCl3 :CH3OH:NH4OH). The solid obtained form the chromatography is recrystallized from CHCl3 :CH3OH to give 901 mg of 5-(4-aminopropyloxyphenyl)-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile as a yellow powder. 1H-NMR (d6 -DMSO): δ 1.80 (t,2H); 2.73 (t,2H); 3.70 (s broad, 2H); 4.03 (t,2H); 6.92 (d,2H); 7.20 (d,2H); 7.85 (s, 1H).