Chlorosuccinimide → HCID 83484369, Verbindung

HRID 874724

Reaktionsgleichung

Reaktionsgleichung von HRID 874724
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.[Cl:13]N1C(=O)CCC1=O>C(#N)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=2)[C:4]([Cl:13])=[CH:3]1

Komponenten

4

Edukt 2

HCID 31398ChlorosuccinimideHCID 75375341-methyl-1H-indole-5-carbaldehyde

Produkt 1

HCID 83484369HCID 83484369, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

N-Methylindol-5-carbaldehyde (400 mg, 2.5 mmol) was dissolved in dry acetonitrile (10 mL) and treated with N-chlorosuccinimide (400 mg, 3.02 mmol), whereupon the solution turned red. The reaction mixture was stirred at room temperature for 20 h. The solvent was removed in vacuum and the residue was purified by column chromatography (silica gel 60). Yield: 300 mg (1.55 mmol, 62%); colorless solid of mp 109° C.; Rf=0.27 (ethyl acetate/n-hexane 1:4); νmax (ATR)/cm−1 3103, 2845, 2751, 1680, 1602, 1454, 1414, 1362, 1343, 1274, 1238, 1196, 1160, 1134, 1111, 981, 894, 796, 717; 1H NMR (300 MHz, CDCl3) δ 3.75 (3H, s), 7.07 (1H, s), 7.32 (1H, d, J=8.6 Hz), 7.76 (1H, dd, J=8.6 Hz, J=1.5 Hz), 8.07 (1H, d, J=1.5 Hz), 10.01 (1H, s); 13C NMR (75.5 MHz, CDCl3) δ 32.9, 106.3, 109.9, 122.0, 123.3, 125.2, 126.9, 129.2, 138.5, 191.7; m/z (EI) 193 (100) [M+], 164 (57), 128 (43), 101 (48), 87 (28).

Aufarbeitung

  1. customThe solvent was removed in vacuum
  2. customthe residue was purified by column chromatography (silica gel 60)

Quellen und Nachweise

ORD-Eintrag
ord-d18b55f0be01450e8ac5478535d6d460
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980933B2

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