O-Toluidine → 3-Methyl-N-o-tolyl-1H-pyrrole-2-carboxamide

HRID 524972Notes

Reaction equation

HRID 524972 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][NH:4][C:3]=1[C:7]([OH:9])=O.C(Cl)(=O)C(Cl)=O.[NH2:16][C:17]1[C:18]([CH3:23])=[CH:19][CH:20]=[CH:21][CH:22]=1>ClCCl.CN(C=O)C>[CH3:1][C:2]1[CH:6]=[CH:5][NH:4][C:3]=1[C:7]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[O:9]

Participants

6

Reactant 3

HCID 7242O-ToluidineHCID 65578Oxalyl chlorideHCID 71403523-methyl-1H-pyrrole-2-carboxylic acid

Product 1

HCID 709222793-Methyl-N-o-tolyl-1H-pyrrole-2-carboxamideYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

2.0 g (15.98 mmol) of 3-methyl-1H-pyrrole-2-carboxylic acid were dissolved in 50 mL of dichloromethane. 5.60 mL (63.9 mmol) of oxalyl chloride were added, followed by 5 drops of DMF. The reaction mixture was stirred at room temperature for 2 hours and then the solvents were evaporated. The black oil residue was dissolved in 50 mL of dichloromethane and 6.85 g (63.9 mmol) of o-toluidine were added dropwise. The reaction was stirred at room temperature for 1 hour and then the solvent was evaporated. The crude product was purified by flash chromatography (dichloromethane to dichloromethane/methanol 95:5) and then triturated in diisopropylether to give 2.97 g (87% yield) of the title compound as a brown solid.

Workup

  1. customthe solvents were evaporated
  2. dissolutionThe black oil residue was dissolved in 50 mL of dichloromethane
  3. stirringThe reaction was stirred at room temperature for 1 hour
  4. customthe solvent was evaporated
  5. customThe crude product was purified by flash chromatography (dichloromethane to dichloromethane/methanol 95:5)
  6. customtriturated in diisopropylether

Sources & evidence

ORD record
ord-f236cc4087e84bb6a79ccd2afd49b8c4
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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