Hydrochloric Acid → 1-methyl-1H-pyrrole-3-carboxylic acid

HRID 1595157Notes

Reaction equation

HRID 1595157 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]([O:9]CC)=[O:8])=[CH:3]1.[OH-].[Na+].Cl.[Cl-].[Na+]>>[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]([OH:9])=[O:8])=[CH:3]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 11062584Ethyl 1-methyl-1H-pyrrole-3-carboxylate

Product 1

HCID 101540541-methyl-1H-pyrrole-3-carboxylic acidYield 92.2%

Procedure

A mixture of Compound 1 (7.66 g, 50 mmole), which had been obtained in Preparation Example 1, and a 2 N aqueous solution of sodium hydroxide (37.5 ml, 75 mmole) was refluxed for 2 hours. The reaction mixture was cooled to 0° C., to which 6 N hydrochloric acid was added under stirring to acidify the same. Sodium chloride (15 g) was then added, followed by stirring for 1 hour over an ice-acetone bath. Precipitated crystals were collected. Those crystals were washed with chilled water and then dried under reduced pressure, whereby the title compound (5.77 g) was obtained (yield: 92.2%).

Workup

  1. customhad been obtained in Preparation Example 1
  2. additionwas added
  3. stirringby stirring for 1 hour over an ice-acetone bath
  4. customPrecipitated crystals
  5. customwere collected
  6. washThose crystals were washed with chilled water
  7. dry with materialdried under reduced pressure, whereby the title compound (5.77 g)
  8. customwas obtained (yield: 92.2%)

Sources & evidence

ORD record
ord-53a7e84357c245cda9a8ab828ff0f1ed
Source dataset
uspto-grants-2001_09
Patent number
US06288056B1

Reaction notes

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