Potassium Carbonate → HCID 21087562, Verbindung

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Reaktionsgleichung

[CH:1]1[C:13]2[N:12]([CH2:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl[CH:25](Cl)[O:26]C.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.CO.O>[CH3:19][N:17]([CH3:18])[CH2:16][CH2:15][CH2:14][N:12]1[C:11]2[CH:10]=[CH:9][C:8]([CH:25]=[O:26])=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A 100-mL round-bottomed flask was charged with a solution of 3-(9H-carbazol-9-yl)-N,N-dimethylpropan-1-amine (500 mg, 1.98 mmol, 1.00 equiv) in DCM (10 mL), aluminum (III) chloride (550 mg, 4.17 mmol, 2.00 equiv), dichloro(methoxy)methane (0.24 mL, 1.10 equiv), water (10 mL) and K2CO3 (20 mL). The resulting mixture was stirred at 0° C. for 20 hours. The reaction progress was monitored by TLC (DCM: MeOH=10:1). Upon completion, the resulting solution was extracted with ethyl acetate (3×30 mL). Combined organic layers were dried over anhydrous sodium sulfate and concentrated on a rotary evaporator affording 9-(3-(dimethylamino)propyl)-9H-carbazole-3-carbaldehyde as yellow oil (0.45 g, 81%).

Aufarbeitung

extractionUpon completion, the resulting solution was extracted with ethyl acetate (3×30 mL)
dry with materialCombined organic layers were dried over anhydrous sodium sulfate
concentrationconcentrated on a rotary evaporator

Quellen und Nachweise

ORD-Eintrag: ord-a2e075ffd212454cac68fac13649508c
Quelldatensatz: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08080566B1

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