Methyl iodide → Methyl 1-methyl-1H-indazole-3-carboxylate

HRID 846596

Reaktionsgleichung

Reaktionsgleichung von HRID 846596
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][N:6]=1)=[O:4].[H-].[Na+].[H][H].[CH3:18]I>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH3:18])[N:6]=1)=[O:4]

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 657476methyl 1H-indazole-3-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 13900574Methyl 1-methyl-1H-indazole-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of indazole-3-carboxylic acid methyl ester (2.76 g, 0.0159 mole) in dry dimethylformamide (20 ml) was added dropwise to a stirred suspension of 60% sodium hydride (oil dispersion) (0.67 g, 0.0176 mole) in dimethylformamide (50 ml). After the addition was completed and the evolution of the hydrogen ceased, the mixture was heated to 80° C. and then cooled to ambient temperature. A solution of methyl iodide (4.23 g, 0.030 mole) in dimethylformamide (10 ml) was added dropwise to the stirred reaction mixture. After stirring for 15 minutes, the mixture was warmed to 50° C. for 30 minutes, and then cooled to ambient temperature. The reaction mixture was diluted to a volume of 300 ml with ice/water and extracted with two 100 ml portions of methylene chloride. The extract was dried (magnesium sulfate), and concentrated to an oil. Dimethylformamide was distilled from the mixture and the residual oil was triturated with petroleum ether to obtain a solid. The solid (1.66 g, 55%) was collected by filtration and recrystallized from isooctane to give 1.20 g; mp 78°-79° C.

Aufarbeitung

  1. additionAfter the addition
  2. temperaturecooled to ambient temperature
  3. temperaturethe mixture was warmed to 50° C. for 30 minutes
  4. temperaturecooled to ambient temperature
  5. extractionextracted with two 100 ml portions of methylene chloride
  6. dry with materialThe extract was dried (magnesium sulfate)
  7. concentrationconcentrated to an oil
  8. distillationDimethylformamide was distilled from the mixture
  9. customthe residual oil was triturated with petroleum ether
  10. customto obtain a solid
  11. filtrationThe solid (1.66 g, 55%) was collected by filtration
  12. customrecrystallized from isooctane
  13. customto give 1.20 g

Quellen und Nachweise

ORD-Eintrag
ord-2a4b0acd3eb14b7c94eb24608747791b
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05137895

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