Methylamine → N,1-dimethyl-1H-indole-3-carboxamide

HRID 1921005Notes

Reaction equation

HRID 1921005 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([O:13]C)=O)=[CH:3]1.[CH3:15][NH2:16]>>[CH3:15][NH:16][C:11]([C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:2]([CH3:1])[CH:3]=1)=[O:13]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 842006Methyl 1-methyl-1H-indole-3-carboxylate

Product 1

HCID 5152277N,1-dimethyl-1H-indole-3-carboxamideYield 56%

Procedure

A suspension of methyl 1-methyl-1H-indole-3-carboxylate (4.30 g, 22.74 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. Flash chromatography on silica gel (ethyl acetate) gave the title compound (2.4 g, 56%) as a white solid: MS (ES) m/e 189 (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

Sources & evidence

ORD record
ord-3897307f888041b6a9c42b08a4b2f9ab
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

Loading…