Hydrogen Peroxide → HCID 49782544, compound

HRID 402305Notes

Reaction equation

HRID 402305 reaction equation
[CH2:1]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=3)=[CH:15][CH:16]=2)[C:11]([CH:25]=[O:26])=[CH:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[K].OO.[O-:30][Mn](=O)(=O)=O.[K+]>CC(C)=O.O>[CH2:1]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=3)=[CH:15][CH:16]=2)[C:11]([C:25]([OH:30])=[O:26])=[CH:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 516875Potassium PermanganateHCID 5462222PotassiumHCID 49782542HCID 49782542, compound

Product 1

HCID 49782544HCID 49782544, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

The method of Andreani, A.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Roda, A.; Guardigli, M.; Traniello, S.; Spisani, S. N-Benzyl-2-chloroindole-3-carboxylic acids as potential anti-inflammatory agents. Synthesis and screening for effects on human neutrophil functions and on COX1/COX2 activity. Eur J Med. Chem. 2004, 39, 785-91, was followed. Compound 9 (0.573 mmol, 1 equiv) was dissolved in 10 mL of acetone and treated with a solution of potassium permanaganate (KMnO4, 1.5 mmol) in water (5 mL). The reaction mixture was stirred at room temperature for 5 h, treated with 10% H2O2 until the pink color of KMnO4 was not observed and then filtered. The solvent was removed under reduced pressure and the resulting residue was filtered again (if necessary), acidified with 2M HCl and extracted with Et2O. The organic solvent was removed in vacuo and the residue was purified by column chromatography with hexane/EtOAc as eluting solvents. Yield: 62%; 1H NMR (300 MHz, CDCl3): δ 8.84 (s, 1 H), 7.92 (s, 1 H), 7.54-7.48 (m, 2 H), 7.41-7.29 (m, 3 H), 7.14 (d, J=6.6 Hz, 1 H), 4.12 (t, J=6.6 Hz, 2 H), 2.44 (s, 3 H), 1.87 (t, J=6.6 Hz, 3 H), 1.37-1.25 (m, 10 H), 0.86 (t, J=6.6 Hz, 3 H); 13C NMR (75 MHz, CDCl3): δ 170.3, 142.3, 141.9, 138.4, 138.2, 136.1, 136.0, 135.8, 128.5, 128.3, 127.4, 124.6, 120.3, 110.3, 106.3, 47.2, 31.7, 31.1, 29.8, 29.1, 22.6, 21.5, 21.5, 14.0.

Workup

  1. customSynthesis
  2. filtrationfiltered
  3. customThe solvent was removed under reduced pressure
  4. filtrationthe resulting residue was filtered again (if necessary)
  5. extractionextracted with Et2O
  6. customThe organic solvent was removed in vacuo
  7. customthe residue was purified by column chromatography with hexane/EtOAc
  8. washas eluting solvents

Sources & evidence

ORD record
ord-dcdaa1a844ac49c2bcb4256c62d0497c
Source dataset
uspto-grants-2014_06
Patent number
US08742100B2

Reaction notes

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