Sodium Hydroxide → HCID 12897089, compound

Methyl 5-chloropyrrole-3-carboxylate (900 g.) was refluxed for 9 hours with 20 ml. of methanol and 10 ml. of 1N 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 evaporated 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.).

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. customevaporated to product (715 mg., m.p. 175°-178° C.)
8. customRecrystallization from methylene chloride/hexane
9. customafforded
10. custompurified 5-chloropyrrole-3-carboxylic acid (300 mg., m.p. 178°-180° C.)

ORD record

ord-d3e8db990aab446fbf256f27927f531a

Source dataset

uspto-grants-1985_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04511576