Sodium Hydroxide → Mcn 2891

HRID 1585619Notes

Reaction equation

HRID 1585619 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%. Found: C, 62.74; H, 5.22; N, 4.47%.

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-b48c11be8ad148dfaf0c582232c3ed21
Source dataset
uspto-grants-1999_08
Patent number
US05939417

Reaction notes

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