Hydrochloric Acid → 3-(2,4-dimethyl-1H-pyrrol-3-yl)propanoic Acid

HRID 1243429Notes

Reaction equation

HRID 1243429 reaction equation
[CH3:1][C:2]1[NH:3][C:4](C(OCC)=O)=[C:5]([CH3:14])[C:6]=1[CH2:7][CH2:8][C:9]([O:11]CC)=[O:10].[OH-].[Na+].Cl>>[C:9]([CH2:8][CH2:7][C:6]1[C:5]([CH3:14])=[CH:4][NH:3][C:2]=1[CH3:1])([OH:11])=[O:10]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 291761Ethyl 2,4-dimethyl-5-(ethoxycarbonyl)-3-pyrrolepropionate

Product 1

HCID 15125193-(2,4-dimethyl-1H-pyrrol-3-yl)propanoic AcidYield 101.2%

Conditions

Temperature
50 °C

Procedure

2,4-Dimethyl-5-ethoxycarbonyl-3-(2-ethoxycarbonylethyl)-pyrrole (1.07 kg) and 3.2 L 5 N sodium hydroxide were mechanically stirred in a 12 L three-neck round bottom flask equipped with a reflux condenser and an addition funnel and heated in an oil bath. The mixture was refluxed for 3 hours after which time the internal temperature was 96° C., all solids were dissolved and thin layer chromatography showed hydrolysis to be complete. The heating bath was removed and the mixture cooled to 50° C. in a water bath. 12N Hydrochloric acid (˜1.3 L) was slowly added. After about 50% of the acid was added gas evolution began and the temperature reached 60° C. As more acid was added, gas evolution increased and a yellow precipitate formed. The final pH was adjusted to 3.5 with hydrochloric acid. The mixture was cooled in an ice bath to 8° C. The solids were collected by vacuum filtration, washed twice with 0.5 L of distilled water and dried for 48 hours in a vacuum oven at 55-60° C. to give 677 g (101% yield) of 3-(2-carboxyethyl)-2,4-dimethylpyrrole.

Workup

  1. customequipped with a reflux condenser and an addition funnel
  2. temperatureheated in an oil bath
  3. temperatureThe mixture was refluxed for 3 hours after which time the internal temperature
  4. customwas 96° C.
  5. dissolutionall solids were dissolved
  6. customhydrolysis
  7. customThe heating bath was removed
  8. addition12N Hydrochloric acid (˜1.3 L) was slowly added
  9. additionAfter about 50% of the acid was added gas evolution
  10. customreached 60° C
  11. additionAs more acid was added
  12. temperaturegas evolution increased
  13. customa yellow precipitate formed
  14. temperatureThe mixture was cooled in an ice bath to 8° C
  15. filtrationThe solids were collected by vacuum filtration
  16. washwashed twice with 0.5 L of distilled water
  17. customdried for 48 hours in a vacuum oven at 55-60° C.

Sources & evidence

ORD record
ord-2da0a78bce3f4be18f166d806a56ffd9
Source dataset
uspto-grants-2006_10
Patent number
US07119090B2

Reaction notes

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