Sodium Hydroxide → Mcn 2891

HRID 1606176Notes

Reaction equation

HRID 1606176 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH:14]([CH3:20])[C:15]([O:17]CC)=[O:16])=[CH:10][C:9]=2[CH3:21])=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH:14]([CH3:20])[C:15]([OH:17])=[O:16])=[CH:10][C:9]=2[CH3:21])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118464ethyl 5-(4-chlorobenzoyl)-alpha,1,4-trimethyl-1H-pyrrole-2-acetate

Product 1

HCID 198126Mcn 2891

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An ethanol solution of 2.9 g. (0.0087 mole) of ethyl 5-(p-chlorobenzoyl)1,4,α-trimethylpyrrole-2-acetate is added to 17.5 ml. 0.5 N sodium hydroxide solution and the mixture is heated under reflux for one hour. The ethanol is evaporated in vacuo and the solution poured into dilute hydrochloric acid. The precipitated solid is collected by filtration and recrystallized from ether-cyclohexane to give 5-(p-chlorobenzoyl)-1,4,α-trimethylpyrrole-2-acetic acid as a white solid, m.p. 153°-154°C. Anal. Calcd. for C16H16ClNO3 : C, 62.85; H, 5.29; N, 4.58%.

Workup

  1. temperatureunder reflux for one hour
  2. customThe ethanol is evaporated in vacuo
  3. additionthe solution poured into dilute hydrochloric acid
  4. filtrationThe precipitated solid is collected by filtration
  5. customrecrystallized from ether-cyclohexane

Sources & evidence

ORD record
ord-40a159cb8b0149f48eebd65449611e79
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

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