Pyrrole-2-Carboxylic Acid → Pyrrole-2-carbonyl chloride

HRID 456655Notes

Reaction equation

HRID 456655 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=[O:7].[C:9](Cl)(=O)[C:10]([Cl:12])=[O:11]>C(Cl)Cl.CN(C=O)C>[CH2:9]([O:7][C:6]([C:2]1[NH:1][CH:5]=[CH:4][CH:3]=1)=[O:8])[CH3:10].[NH:1]1[CH:2]=[CH:3][CH:4]=[C:9]1[C:10]([Cl:12])=[O:11]

Participants

6

Reactant 2

HCID 12473Pyrrole-2-Carboxylic AcidHCID 65578Oxalyl chloride

Product 2

HCID 224558Pyrrole-2-carbonyl chlorideHCID 255670Ethyl 1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1H-pyrrole-2-carboxylic acid ethyl ester was prepared as follows: to a solution of 1H-pyrrole-2-carboxylic acid (10 mmol; Aldrich, Milwaukee, Wis.) in DCM (15 mL) was added oxalyl chloride (10 mmol) and 3 drops of DMF at 0° C. The solution was stirred at 0° C. for 30 minutes to form 1H-pyrrole-2-carbonyl chloride. Ethanol was added and the mixture was stirred at room temperature for 30 minutes. The mixture was concetrated to afford 1-carboxylic acid ethyl ester.

Sources & evidence

ORD record
ord-79c8df14abe64c0da9d97d1536a232aa
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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