Hydrochloric Acid → 1-Methyl-1H-pyrrole-2-acetic acid

HRID 863632Notes

Reaction equation

HRID 863632 reaction equation
C1(C)C=CC(C([C:9]2[N:13]([CH3:14])[C:12](CC#N)=[CH:11][CH:10]=2)=O)=CC=1.[OH-:19].[Na+].Cl.[CH2:22]([OH:24])[CH3:23]>>[CH3:14][N:13]1[CH:9]=[CH:10][CH:11]=[C:12]1[CH2:23][C:22]([OH:19])=[O:24]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 111074051-Methyl-5-(p-toluoyl)pyrrole-2-acetonitrile

Product 1

HCID 890951-Methyl-1H-pyrrole-2-acetic acid

Procedure

A solution of 3.67 g. (0.015 mole) of 5-(ρ-toluoyl)-1-methyl-pyrrole-2-acetonitrile, 24 ml. of 1N sodium hydroxide, and 50 ml. of 95% ethanol is stirred and refluxed for twenty-four hours. The resulting solution is poured into ice acidified with dilute hydrochloric acid. A white solid precipitates which is extracted into ether. The ether phase is washed with a saturated solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent is evaporated and a white solid, 5-ρ-toluoyl)-1-methylpyrrole-2-acetic acid, is obtained which is recrystallized twice from isopropanol, M.P., 155°-157° C.

Workup

  1. temperaturerefluxed for twenty-four hours
  2. additionThe resulting solution is poured into ice
  3. customA white solid precipitates which
  4. extractionis extracted into ether
  5. washThe ether phase is washed with a saturated solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent is evaporated

Sources & evidence

ORD record
ord-f59b27f99f18408296e7291be9a8e9af
Source dataset
uspto-grants-1998_02
Patent number
US05721347

Reaction notes

Loading…