Ammonium Hydroxide → 5-Chloro-6-methoxy-4-methyl-8-nitroquinoline

반응식

[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([N+:15]([O-:17])=[O:16])[CH:8]=[C:9]([O:13][CH3:14])[C:10]=2O)[N:5]=[CH:4][CH:3]=1.[OH-].[NH4+].P(Cl)(Cl)([Cl:22])=O>>[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([N+:15]([O-:17])=[O:16])[CH:8]=[C:9]([O:13][CH3:14])[C:10]=2[Cl:22])[N:5]=[CH:4][CH:3]=1

참가 물질

반응물 3

HCID 14923Ammonium Hydroxide

HCID 24813Phosphorus oxychloride

HCID 1357785114-Methyl-5-hydroxy-6-methoxy-8-nitroquinoline

생성물 1

HCID 120499275-Chloro-6-methoxy-4-methyl-8-nitroquinoline수율 69%

실험 절차

A solution of the 5-hydroxyquinoline IV (5.25 g, 0.022 mol) in phosphorus oxychloride (75 mL) was heated at 80° for 2 hours. The reaction mixture was poured onto ice and basified with excess ammonium hydroxide. The tan solid was filtered to give 5.8 g of crude product. This material was purified via column chromatography over silica gel and elution with chloroform. The fast-moving yellow band was collected and concentrated to give 3.9 g (69%) of the title compound, mp 167°-169°. Crystallization from ethanol did not raise the melting point. The crude material can also be purified by sublimation.