Sodium Hydroxide → HCID 12897089, compound

HRID 894071Notes

Reaction equation

HRID 894071 reaction equation
[Cl:1][C:2]1[NH:6][CH:5]=[C:4]([C:7]([O:9]C)=[O:8])[CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[NH:6][CH:5]=[C:4]([C:7]([OH:9])=[O:8])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12897088HCID 12897088, compound

Product 1

HCID 12897089HCID 12897089, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 5-chloropyrrole-3-carboxylate (900 g.) was refluxed for 9 hours with 20 ml. of methanol and 10 ml. of 1 N sodium hydroxide. Methanol was removed by evaporation, the aqueous residue was diluted with approximately 10 ml. of water and extracted twice with ether. The aqueous phase was acidified with conc. hydrochloric acid and product extracted into ethyl acetate. The three ethyl acetate extracts were combined, washed with saturated sodium chloride, dried over anhydrous sodium sulfate and evaported to product (715 mg., m.p. 175°-178° C.). Recrystallization from methylene chloride/hexane afforded purified 5-chloropyrrole-3-carboxylic acid (300 mg., m.p. 178°-180° C.).

Workup

  1. customMethanol was removed by evaporation
  2. additionthe aqueous residue was diluted with approximately 10 ml
  3. extractionof water and extracted twice with ether
  4. extractionextracted into ethyl acetate
  5. washwashed with saturated sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customRecrystallization from methylene chloride/hexane
  8. customafforded
  9. custompurified 5-chloropyrrole-3-carboxylic acid (300 mg., m.p. 178°-180° C.)

Sources & evidence

ORD record
ord-0d5950d80ec64e7a9af10fac8540442c
Source dataset
uspto-grants-1981_08
Patent number
US04282242

Reaction notes

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