Methyl iodide → Methyl 4-chloro-1,2-dimethyl-1H-indole-3-carboxylate

HRID 453854Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 453854
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([C:12]([O:14][CH3:15])=[O:13])=[C:5]([CH3:11])[NH:6]2.[H-].[Na+].[CH3:18]I>CN(C=O)C.[NH4+].[Cl-]>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([C:12]([O:14][CH3:15])=[O:13])=[C:5]([CH3:11])[N:6]2[CH3:18]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59473719methyl 4-chloro-2-methyl-1H-indole-3-carboxylate

Produkt 1

HCID 59473668Methyl 4-chloro-1,2-dimethyl-1H-indole-3-carboxylateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

Methyl 4-chloro-2-methyl-1H-indole-3-carboxylate (13.45 mmol, 1.0 equiv.) was dissolved in DMF (7 ml) and added at 0° C. to a suspension of NaH (26.90 mmol, 2.0 equiv.) in DMF (13 ml). The mixture was then stirred for 30 min. Methyl iodide (20.17 mmol, 1.5 equiv.) was added dropwise at 0° C. and stirring was carried out for 2 h at 25° C. The reaction mixture was diluted with NH4Cl solution (20 ml) and extracted with ethyl acetate (3×50 ml). The combined organic phases were washed with water and sat. NaCl solution (in each case 50 ml), dried over Na2SO4 and concentrated to dryness under reduced pressure. Yield: 72%

Aufarbeitung

  1. stirringstirring
  2. waitwas carried out for 2 h at 25° C
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. washThe combined organic phases were washed with water and sat. NaCl solution (in each case 50 ml),
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7daa7349e05845bdb1ec6c47cb131807
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492559B2

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