Sodium Hydroxide → HCID 12897067, compound

HRID 1980923Notes

Reaction equation

HRID 1980923 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:3]=1[C:4]([C:6]1[NH:10][CH:9]=[C:8]([C:11]([O:13]C)=[O:12])[CH:7]=1)=[O:5].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:3]=1[C:4]([C:6]1[NH:10][CH:9]=[C:8]([C:11]([OH:13])=[O:12])[CH:7]=1)=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12897066HCID 12897066, compound

Product 1

HCID 12897067HCID 12897067, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 5-(2,4-dichlorobenzoyl)pyrrole-3-carboxylate (3.0 g.) was refluxed for 2.5 hours in 35 ml. of methanol and 35 ml. of 1N sodium hydroxide. The methanol was evaporated, and approximately one volume of water was added to the aqueous residue. The mixture was extracted twice with ether, and acidified with conc. hydrochloric acid to yield 2.12 g. of crude product, recovered by filtration. Recrystallization from methanol, which included an activated carbon treatment, afforded purified 5-(2,4-dichlorobenzoyl)pyrrole-3-carboxylic acid (1.06 g., m.p. 245°-249° C.).

Workup

  1. customThe methanol was evaporated
  2. additionapproximately one volume of water was added to the aqueous residue
  3. extractionThe mixture was extracted twice with ether
  4. customto yield 2.12 g
  5. filtrationof crude product, recovered by filtration
  6. customRecrystallization from methanol, which
  7. customafforded
  8. custompurified 5-(2,4-dichlorobenzoyl)pyrrole-3-carboxylic acid (1.06 g., m.p. 245°-249° C.)

Sources & evidence

ORD record
ord-616188895cca4aa5becb582aba6ad3f7
Source dataset
uspto-grants-1985_04
Patent number
US04511575

Reaction notes

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