N-methyl-1H-indole-2-carboxamide → N-Methyl-1H-indole-2-methanamine

HRID 1710519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1710519
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][NH:8][C:9]([C:11]1[NH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)=O>C1COCC1>[CH3:7][NH:8][CH2:9][C:11]1[NH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2

Komponenten

4

Edukt 2

HCID 12461785N-methyl-1H-indole-2-carboxamideHCID 21226445Aluminium lithium hydride2×

Produkt 1

HCID 11194490N-Methyl-1H-indole-2-methanamineAusbeute 510,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of LiAlH4 in THF (1.0 M, 250 mL, 250 mmole) was slowly added via syringe to a solution of N-methyl-1H-indol-2-carboxamide (21.50 g, 12.34 mmole) in anhydrous THF (100 mL). Gas was evolved during the addition of the first 50 mL of LiAlH4 solution. When the addition was complete, the resulting light yellow solution was heated at gentle reflux. After 23 hr, the reaction was cooled in ice and quenched by the sequential dropwise addition of H2O (9.5 mL), 1.0 N NaOH (20 mL), and H2O (28.5 mL). The mixture was stirred for 15 min, then was filtered through Celite®, and the filter pad was washed thoroughly with THF. The filtrate was concentrated and the residue was flash chromatographed on silica gel (10% MeOH/CHCl3 containing 0.5% cone. NH4OH). The title compound (10.10 g, 51%) was obtained as a light yellow oil: MS (ES) m/e 161 (M+H)+.

Aufarbeitung

  1. additionWhen the addition
  2. temperaturethe resulting light yellow solution was heated at gentle reflux
  3. temperaturethe reaction was cooled in ice
  4. customquenched by the sequential dropwise addition of H2O (9.5 mL), 1.0 N NaOH (20 mL), and H2O (28.5 mL)
  5. filtrationwas filtered through Celite®
  6. washthe filter pad was washed thoroughly with THF
  7. concentrationThe filtrate was concentrated
  8. customchromatographed on silica gel (10% MeOH/CHCl3 containing 0.5% cone. NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-80fb9910ce2c4e2f94f8f8f6cf12622a
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790716B2

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