Hydrochloric Acid → 5-phenyl-1H-pyrrole-2-carboxylic acid

HRID 1178114Notes

Reaction equation

HRID 1178114 reaction equation
[Li+].[OH-].C([O:5][C:6]([C:8]1[NH:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:12]=1)=[O:7])C.O.Cl>C1COCC1.CO.O>[C:13]1([C:10]2[NH:9][C:8]([C:6]([OH:7])=[O:5])=[CH:12][CH:11]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 12378033Ethyl 5-phenyl-1H-pyrrole-2-carboxylate

Product 1

HCID 2261995-phenyl-1H-pyrrole-2-carboxylic acidYield 63.8%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

LiOH (27.5 mg, 0.65 mmol) was added to a stirred solution of 5-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester (67 mg, 0.31 mmol) in THF:MeOH:H2O (3:1:1, 3 mL), and the resulting mixture was stirred at room temperature for 2 hrs. The reaction mixture was concentrated under reduced pressure to get the residue. Cold water was then added and acidified it with 10% aqueous HCl, filtered the solid precipitated to afford 37 mg (63.79% yield) of 5-Phenyl-1H-pyrrole-2-carboxylic acid. LCMS Purity: 92.24%.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto get the residue
  3. filtrationfiltered the solid
  4. customprecipitated

Sources & evidence

ORD record
ord-e27307d9248e4ec38b10f4b244154c0f
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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