Methylamine → N-Methyl-1H-pyrrole-2-carboxamide

HRID 456658Notes

Reaction equation

HRID 456658 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.C(Cl)(=O)C(Cl)=O.[CH3:15][NH2:16]>C(Cl)Cl.CN(C=O)C.N1C=CC=C1C(Cl)=O.C(OCC)(=O)C>[CH3:15][NH:16][C:6]([C:2]1[NH:1][CH:5]=[CH:4][CH:3]=1)=[O:8]

Participants

8

Reactant 3

HCID 6329MethylamineHCID 12473Pyrrole-2-Carboxylic AcidHCID 65578Oxalyl chloride

Product 1

HCID 23273389N-Methyl-1H-pyrrole-2-carboxamide

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 224558Pyrrole-2-carbonyl chlorideSolvent

Procedure

To a solution of 1H-pyrrole-2-carboxylic acid (1 g, 9 mmol) (Aldrich, Milwaukee, Wis.) in DCM (15 mL) was added oxalyl chloride (1.1 mL) and DMF (3 drops). The mixture was stirred at room temperature resulting in 1H-pyrrole-2-carbonyl chloride. Methylamine (30 mmol) was then added to the acid chloride and the mixture was stirred at room temperature. The reaction was diluted with ethyl acetate, washed with brine (2×), NaHCO3, dried and concentrated to give 1H-pyrrole-2-carboxylic acid methylamide.

Workup

  1. stirringthe mixture was stirred at room temperature
  2. washwashed with brine (2×), NaHCO3
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b651e65a5daa42c48177d12dc97e29c8
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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