Hydrochloric Acid → 4-phenyl-1H-pyrrole-2-carboxylic acid

HRID 1178117Notes

Reaction equation

HRID 1178117 reaction equation
[Li+].[OH-].C([O:5][C:6]([C:8]1[NH:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=1)=[O:7])C.O.Cl>C1COCC1.CO.O>[C:13]1([C:11]2[CH:12]=[C:8]([C:6]([OH:7])=[O:5])[NH:9][CH:10]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 14643813Ethyl 4-phenyl-1H-pyrrole-2-carboxylate

Product 1

HCID 128971004-phenyl-1H-pyrrole-2-carboxylic acidYield 83.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

LiOH (180 mg, 4.3 mmol) was added to a stirred solution of 4-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester (143 mg, 0.66 mmol) in THF:MeOH:H2O (3:1:1, 5 mL), and the resulting mixture was stirred at room temperature for 8 hrs. The reaction mixture was concentrated under reduced pressure to get the residue. Cold water was then added and acidified it with concentrated HCl, filtered the solid precipitated to afford 103 mg (83.06% yield) of 4-Phenyl-1H-pyrrole-2-carboxylic acid.

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-0fffb217e08f442b921fbebb8c490f41
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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