Sodium Hydroxide → HCID 18424178, compound

HRID 1282364Notes

Reaction equation

HRID 1282364 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([O:17]CC)=[O:16])=[CH:10][C:9]=2[CH2:20][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]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][C:9]=2[CH2:20][CH3:21])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18424297HCID 18424297, compound

Product 1

HCID 18424178HCID 18424178, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 4.5 g. (0.0136 mole) of ethyl 5-(p-chlorobenzoyl)-4-ethyl-1-methylpyrrole-2-acetate in 28 ml. 0.5 N sodium hydroxide and 1 ml. of ethanol is heated under reflux for 30 minutes. The mixture is then poured into ice-dilute hydrochloric acid. The precipitated solid is filtered, air dried and recrystallized from 2-propanol to give 5-(p-chlorobenzoyl)-4-ethyl-1-methylpyrrole-2-acetic acid as a white solid, m.p. 129-131° C. Anal. Calcd. for C16H16ClNO3: C, 62.85; H, 5.29; N, 4.5%. Found: C, 62.58; H, 5.40; N, 4.83%.

Workup

  1. additionA suspension of 4.5 g
  2. temperatureunder reflux for 30 minutes
  3. additionThe mixture is then poured into ice-dilute hydrochloric acid
  4. filtrationThe precipitated solid is filtered
  5. customair dried
  6. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-8cdc7f5b850c4ded94053f5e557d4c2c
Source dataset
uspto-grants-2002_09
Patent number
US06455703B2

Reaction notes

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