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

HRID 2112652Notes

Reaction equation

HRID 2112652 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-c3d16cce9ae54679831c38a12b574f8c
Source dataset
uspto-grants-2009_04
Patent number
US07524843B2

Reaction notes

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