6-Phenoxynicotinaldehyde → 2-phenoxy-5-((2-(pyridin-3-yl)-5,6-dihydropyridin-3(4H)-ylidene)methyl)pyridine dihydrochloride

HRID 1444749

Reaktionsgleichung

[Cl-:1].[NH3+:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:10]=[NH+:11][CH:12]=[CH:13][CH:14]=1)=O.[Cl-].[O:16]([C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][N:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)(C)C>[ClH:1].[ClH:1].[O:16]([C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[C:6]2[CH2:5][CH2:4][CH2:3][N:2]=[C:7]2[C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[CH:25][N:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

3-(5-Ammoniopentanoyl)pyridinium chloride (101 mg, 0.40 mmol) and 6-phenoxynicotinaldehyde (120 mg, 0.60 mmol) were combined in a reaction vessel and treated with isopropanol (15 mL). The reaction vessel was sealed and the reaction was heated to 80° C. with stirring overnight. The reaction was then cooled to room temperature. The precipitate that formed was recovered by vacuum filtration and washed with a 20% solution of isopropanol in hexane and then with ether. The recovered solid was then dried under vacuum giving 122 mg (73%) of a pale yellow solid. LC-MS: RT=5.08 min, [M+H]+=342.1.

Aufarbeitung

customThe reaction vessel was sealed
temperatureThe reaction was then cooled to room temperature
customThe precipitate that formed
filtrationwas recovered by vacuum filtration
washwashed with a 20% solution of isopropanol in hexane
customThe recovered solid was then dried under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-ae0f567c7dfb4e0f9b94302d12f9c479
Quelldatensatz: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07662965B2

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