Sodium Hydroxide → 3-methyl-1H-pyrrole-2-carboxylic acid

HRID 1052343Notes

Reaction equation

HRID 1052343 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][NH:4][C:3]=1[C:7]([O:9]C)=[O:8].[OH-].[Na+]>CO>[CH3:1][C:2]1[CH:6]=[CH:5][NH:4][C:3]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 24271768methyl 3-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 71403523-methyl-1H-pyrrole-2-carboxylic acidYield 79.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 3-methyl-1H-pyrrole-2-carboxylate (10 g, 0.07 mol, purchased at Aurora Building Blocks, reference number A00.567.027) was dissolved in 200 mL methanol and a solution of sodium hydroxide (2N, 108 mL, 0.22 mol) was added. The mixture was heated at 60° C. overnight. The solvent was evaporated and the residue was acidified to pH 2-3 with 2N hydrochloric acid. A white precipitate was formed and filtered and washed with cool water. The solid was dried in a vacuum oven to give 6.97 g (77% yield) of the desired compound. Purity 100%.

Workup

  1. customThe solvent was evaporated
  2. customA white precipitate was formed
  3. filtrationfiltered
  4. washwashed with cool water
  5. customThe solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-bd9bb909cbe54266bf4d0680afc49a32
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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