Ethanol → 4-[3-(2-Hydrazino-quinolin-6-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

Reaktionsgleichung

Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12][C:13]3[CH:14]=[C:15]([C:19]4([C:25]#[N:26])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[CH:16]=[CH:17][CH:18]=3)[CH:8]=2)[N:3]=1.CCO.O.[NH2:31][NH2:32]>>[NH:31]([C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12][C:13]3[CH:14]=[C:15]([C:19]4([C:25]#[N:26])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[CH:16]=[CH:17][CH:18]=3)[CH:8]=2)[N:3]=1)[NH2:32]

Komponenten

Edukt 3

HCID 702Ethanol

HCID 24654Hydrazine hydrate (1:1)

HCID 582577564-[3-(2-Chloro-quinolin-6-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

Produkt 1

HCID 582577744-[3-(2-Hydrazino-quinolin-6-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

Versuchsvorschrift

5h (4.4 g, 11.6 mmol) was suspended in hydrazine hydrate (11 mL) and EtOH (45 mL) and heated to 80° C. overnight. The reaction was cooled to room temperature and concentrated, and then diluted with EtOAc and water. The aqueous layer was extracted with EtOAc twice, and the combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was dissolved in CH2Cl2 (15 mL) and heated to dissolve as much of the material as possible. Hexanes (45 mL) was added slowly, and the mixture was stirred for 30 minutes. The precipitate was filtered, rinsed with hexanes, and dried to give the desired product, 5i.