Methyl iodide → 1-Methyl-1H-indole-6-carboxylic acid

HRID 20980

Reaktionsgleichung

Reaktionsgleichung von HRID 20980
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH3:15]I.[OH-].[K+]>CN(C=O)C.O>[CH3:15][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 24758Sodium hydrideHCID 5952301H-indole-6-carboxylic acid

Produkt 1

HCID 198192611-Methyl-1H-indole-6-carboxylic acidAusbeute 214,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In a similar manner to Step 1 of Reference Example 12, indole-6-carboxylic acid (200 mg, 1.24 mmol) was dissolved in DMF (2 mL), and the solution was treated with 60% sodium hydride-mineral oil dispersant (109 mg, 2.71 mmol), methyl iodide (0.258 mL, 0.410 mmol) and 4 mol/L aqueous potassium hydroxide solution (2 mL). The reaction mixture was added with water and separated into aqueous layer and organic layer, and the organic layer was removed. The aqueous layer was added with 1 mol/L hydrochloric acid to adjust the pH to 1, followed by stirring at room temperature for 1 hour. The obtained solid was collected by filtration and dried under reduced pressure to obtain 1-methylindole-6-carboxylic acid (154 mg, yield 71%).

Aufarbeitung

  1. customseparated into aqueous layer and organic layer
  2. customthe organic layer was removed
  3. additionThe aqueous layer was added with 1 mol/L hydrochloric acid
  4. filtrationThe obtained solid was collected by filtration
  5. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a5aefe6165594ef5bfe0f2092a468033
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

Verknüpfte Notizen

Wird geladen…