Methylamine → N-methyl-1H-indole-2-carboxamide

HRID 1920999Notes

Reaction equation

HRID 1920999 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12]CC)=O.[CH3:15][NH2:16]>>[CH3:15][NH:16][C:10]([C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:12]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 12461785N-methyl-1H-indole-2-carboxamide

Procedure

A suspension of ethyl indole-2-carboxylate (25.30 g, 133.7 mmole) in 40% aqueous CH3NH2 (400 mL) was stirred at RT. The flask was tightly stoppered to keep the material inside the flask. As the reaction proceeded the product began to precipitate. The reaction was stirred at RT for 3 days, then was concentrated to remove approximately 200 mL of the solvent. The remaining residue was diluted with H2O (500 mL), and the solid was collected by suction filtration and washed with H2O. Drying under high vacuum left the title compound (21.50 g, 92%) as a light yellow solid: MS (ES) m/e 175 (M+H)+.

Workup

  1. customto precipitate
  2. stirringThe reaction was stirred at RT for 3 days
  3. concentrationwas concentrated
  4. customto remove approximately 200 mL of the solvent
  5. additionThe remaining residue was diluted with H2O (500 mL)
  6. filtrationthe solid was collected by suction filtration
  7. washwashed with H2O
  8. customDrying under high vacuum
  9. waitleft the title compound (21.50 g, 92%) as a light yellow solid

Sources & evidence

ORD record
ord-15a5291e42524e638cd7604d346a6bb5
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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