Pyridine → 2-chloro-1-phenyl-1H-indole-3-carbaldehyde

HRID 751324

Reaktionsgleichung

P(Cl)(Cl)([Cl:3])=O.CN([CH:9]=[O:10])C.[C:11]1([N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][C:18]2=O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N1C=CC=CC=1>ClCCl.C(Cl)(Cl)Cl>[Cl:3][C:18]1[N:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:25]2[C:20]([C:19]=1[CH:9]=[O:10])=[CH:21][CH:22]=[CH:23][CH:24]=2

Komponenten

Reaktionsbedingungen

Temperatur: 5 °C

Versuchsvorschrift

Phosphorous oxychloride (50 mL, 538 mmol) is added slowly to a solution of DMF (50 mL) in dichloromethane (50 mL) maintaining the temperature at 5° C. After 30 min, a solution of 1-phenyl-1H-indol-2-one (25 g, 120 mmol) and pyridine (25 mL, 309 mmol) in chloroform (125 mL) is added and the reaction is stirred 48 hr at room temperature. The reaction is poured into ice water (600 mL) and the aqueous layer is separated and extracted with chloroform (3×200 mL). The combined organic layer and extracts is dried, filtered and concentrated. The solid residue is crystallized from ethanol to afford 2-chloro-1-phenyl-1H-indole-3-carboxaldehyde (12.0 g, 39.25% yield) as an orange solid. NMR (CDCl3) 10.21 (1H, s), 8.37 (1H, d), 7.60 (3H, m), 7.41 (2H, m), 7.38 (1H, t), 7.28 (1H, m), 7.10 (1H, d). A second crop (7.5 g, 24.5% yield) is obtained by concentration of the filtrate and chromatography the residue eluting with dichloromethane.

Aufarbeitung

customthe aqueous layer is separated
extractionextracted with chloroform (3×200 mL)
customThe combined organic layer and extracts is dried
filtrationfiltered
concentrationconcentrated
customThe solid residue is crystallized from ethanol

Quellen und Nachweise

ORD-Eintrag: ord-5472b8fb5bd142229321e325dc561d1f
Quelldatensatz: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07405300B2

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