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

HRID 2112653Notes

Reaction equation

HRID 2112653 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 11194490N-Methyl-1H-indole-2-methanamineYield 510.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-a22239374386440f986385ed78d2862a
Source dataset
uspto-grants-2009_04
Patent number
US07524843B2

Reaction notes

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