Water → 2-Chloro-1-methyl-1H-indole-3-carbaldehyde

HRID 751331

Reaktionsgleichung

Reaktionsgleichung von HRID 751331
[Cl:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[H-].[Na+].[CH3:15]I.O>CN(C=O)C>[Cl:1][C:2]1[N:3]([CH3:15])[C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3147912-chloro-1H-indole-3-carbaldehyde

Produkt 1

HCID 3147922-Chloro-1-methyl-1H-indole-3-carbaldehydeAusbeute 108,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-chloro-1H-indole-3-carboxaldehyde (1.0 g, 5.5 mmol) in DMF (30 mL) is treated portionwise over 10 min with 60% sodium hydride (440 mg, 11 mmol). After stirring for 30 min, methyl iodide (685 μL, 11 mmol) is slowly added and the resulting mixture is stirred 3 hr at room temperature. Water (5 mL) is cautiously added and the solvents are removed. The residue is dissolved in ethyl acetate and washed with water, with brine, dried, filtered and concentrated to give 2-chloro-1-methyl-1H-indole-3-carboxaldehyde (1.16 g, 105%), mp 94.5-95.5° C., as a white solid. MS 194 (M+H).

Aufarbeitung

  1. stirringthe resulting mixture is stirred 3 hr at room temperature
  2. customthe solvents are removed
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washwashed with water, with brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-db7c0c23a38e4024ba0f91b3d240dd7d
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405300B2

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