Hydrochloric Acid → 4-chloro-1-methyl-1H-pyrrole-2-carboxylic acid

HRID 499809Notes

Reaction equation

HRID 499809 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([O:10]C)=[O:9])[N:5]([CH3:7])[CH:6]=1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([OH:10])=[O:9])[N:5]([CH3:7])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14102688HCID 14102688, compound

Product 1

HCID 91152664-chloro-1-methyl-1H-pyrrole-2-carboxylic acidYield 92.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-chloro-1-methyl-1H-pyrrole-2-carboxylate (130 mg, 0.75 mmol) in MeOH (4 mL), aq. 1N NaOH (3 mL) was added. After being stirred at room temperature overnight, the mixture was acidified with 1N HCl to pH 1-2. The product was extracted with EtOAc. The EtOAc phase was separated, dried over Na2SO4, concentrated in vacuo to give 4-chloro-1-methyl-1H-pyrrole-2-carboxylic acid as a solid (111 mg).

Workup

  1. extractionThe product was extracted with EtOAc
  2. customThe EtOAc phase was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a9fc0bcdbce040489d182d6821095d6b
Source dataset
uspto-grants-2010_08
Patent number
US07767697B2

Reaction notes

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