Lithium iodide → 1-(4-nitrophenylsulfonyl)-1H-pyrrole-2-carboxylic acid

HRID 59727Notes

Reaction equation

HRID 59727 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH:17]=[CH:16][CH:15]=[C:14]2[C:18]([O:20]C)=[O:19])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[I-].[Li+]>N1C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH:17]=[CH:16][CH:15]=[C:14]2[C:18]([OH:20])=[O:19])(=[O:11])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 86703835methyl 1-(4-nitrophenylsulfonyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 867038341-(4-nitrophenylsulfonyl)-1H-pyrrole-2-carboxylic acidYield 82.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl 1-(4-nitrophenylsulfonyl)-1H-pyrrole-2-carboxylate (Int. 4) (550 mg, 1.773 mmol) in pyridine (25 ml), lithium iodide (1661 mg, 12.41 mmol) was added and the resulting mixture was refluxed for 8 hours. The solution was concentrated under vacuum and the crude was dissolved in DCM (150 ml) and washed with 1N HCl (50 ml×2) and then with brine (50 ml); the organic layer was dried over sodium sulfate and the solvent was removed affording 1-(4-nitrophenylsulfonyl)-1H-pyrrole-2-carboxylic acid (Int. 5) (433 mg, 1.462 mmol).

Workup

  1. temperaturethe resulting mixture was refluxed for 8 hours
  2. concentrationThe solution was concentrated under vacuum
  3. dissolutionthe crude was dissolved in DCM (150 ml)
  4. washwashed with 1N HCl (50 ml×2)
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-28c544d32ed047e4b1cf1ee63257ed24
Source dataset
uspto-grants-2016_09
Patent number
US09440954B2

Reaction notes

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