Hydrochloric Acid → 4-Tridecylpyrrole-2-carboxylic acid

HRID 1090744Notes

Reaction equation

HRID 1090744 reaction equation
[CH2:1]([C:14]1[CH:15]=[C:16]([C:19]([O:21]C)=[O:20])[NH:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C(O)C.[OH-].[Na+].Cl>O>[CH2:1]([C:14]1[CH:15]=[C:16]([C:19]([OH:21])=[O:20])[NH:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 15023274Methyl 4-tridecylpyrrole-2-carboxylate

Product 1

HCID 99480484-Tridecylpyrrole-2-carboxylic acidYield 78.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 10.01 g (32.6 mmol) of methyl 4-tridecylpyrrole-2-carboxylate prepared in Example 32 were added 200 ml of ethanol, 80 ml of water and 5.5 g (131 mmol) of 95% sodium hydroxide and the resulting mixture was heated under reflux for 1 hour. After cooling, 100 ml of water was added thereto. The resulting mixture was acidified with hydrochloric acid and extracted with a mixed solvent of 400 ml of ethyl ether, 100 ml of ethyl acetate and 300 ml of tetrahydrofuran. An aqueous layer was extracted again with 100 ml of ethyl acetate. Then both extracts were combined, washed with a saturated solution of sodium chloride and dried over anhydrous magnesium sulfate. After concentrating the resulting solution under reduced pressure, the recrystallization of the product from a mixed solvent of hexane and tetrahydrofuran gave 7.55 g of 4-tridecylpyrrole-2-carboxylic acid as white crystals, m.p. 150°-151° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter cooling
  4. extractionextracted with a mixed solvent of 400 ml of ethyl ether, 100 ml of ethyl acetate and 300 ml of tetrahydrofuran
  5. extractionAn aqueous layer was extracted again with 100 ml of ethyl acetate
  6. washwashed with a saturated solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationAfter concentrating the resulting solution under reduced pressure
  9. customthe recrystallization of the product from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record
ord-7aaae24d4b0f48ec95c22b0e0565f75c
Source dataset
uspto-grants-1992_01
Patent number
US05082856

Reaction notes

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