Lithium iodide → N-(3,4-dichlorophenylsulphonyl)-5-hydroxyindole-2-carboxylic acid

HRID 1582647Notes

Reaction equation

HRID 1582647 reaction equation
[I-].[Li+].C[O:4][C:5]([C:7]1[N:8]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)(=[O:19])=[O:18])[C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([OH:16])=[CH:11][CH:10]=2)=[O:6]>N1C=CC=CC=1>[Cl:27][C:22]1[CH:21]=[C:20]([S:17]([N:8]2[C:9]3[C:14](=[CH:13][C:12]([OH:16])=[CH:11][CH:10]=3)[CH:15]=[C:7]2[C:5]([OH:6])=[O:4])(=[O:18])=[O:19])[CH:25]=[CH:24][C:23]=1[Cl:26]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 22718735Methyl n-(3,4-dichlorophenylsulphonyl)-5-hydroxyindole-2-carboxylate

Product 1

HCID 9843144N-(3,4-dichlorophenylsulphonyl)-5-hydroxyindole-2-carboxylic acidYield 29%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of anhydrous lithium iodide (870 mg) and methyl_N-(3,4-dichlorophenylsulphonyl)-5-hydroxyindole-2-carboxylate (260 mg) in pyridine (15 ml) was stirred at reflux for 4 hours. The reaction was cooled and concentrated in vacuo. The residue was dissolved in water (20 ml) and acidified with acetic acid. The product was extracted with ethyl acetate and the combined extracts were dried, concentrated in vacuo and the residue purified by column chromatography using dichloromethane-50% ethyl acetate containing 1% acetic acid as eluent to give the desired product as a glass (72 mg, 29%). NMR: δ 6.9 (m, 2H), 7.25 (s, 1H), 7.85 (d, 1H), 7.9 (m, 2H), 8.15 (s, 1H), 9.5 (s, 1H); m/z 385.8 (M−H−). The starting material was prepared by

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in water (20 ml)
  5. extractionThe product was extracted with ethyl acetate
  6. customthe combined extracts were dried
  7. concentrationconcentrated in vacuo
  8. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-9c198956fc244bcbaeac42e96b8c3240
Source dataset
uspto-grants-2004_05
Patent number
US06737435B1

Reaction notes

Loading…