Potassium Permanganate → 5-(4,6-Dimethoxypyrimidin-2-yl)oxy-3-methylbenzothiophene-4-carboxylic acid

HRID 51994Notes

Reaction equation

HRID 51994 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:13]=[CH:14][C:15]3[S:19][CH:18]=[C:17]([CH3:20])[C:16]=3[C:21]=2[CH:22]=[O:23])[N:4]=1.[Mn]([O-])(=O)(=O)=[O:25].[K+]>CC(C)=O.O>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([O:11][C:12]2[C:21]([C:22]([OH:25])=[O:23])=[C:16]3[C:17]([CH3:20])=[CH:18][S:19][C:15]3=[CH:14][CH:13]=2)[N:6]=1

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 190772825-(4,6-Dimethoxypyrimidin-2-yl)oxy-4-formyl-3-methylbenzothiophene

Product 1

HCID 199627855-(4,6-Dimethoxypyrimidin-2-yl)oxy-3-methylbenzothiophene-4-carboxylic acidYield 76%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

0.6 g of 5-(4,6-dimethoxypyrimidin-2-yl)oxy-4-formyl-3-methylbenzothiophene was dissolved in 80 ml of acetone. While stirring the solution at room temperature, 0.6 g of potassium permanganate dissolved in 10 ml of water was dropwise added thereto over a period of 15 minutes, and the mixture was further stirred at room temperature for 4 hours. It was then concentrated under reduced pressure to remove acetone, and then a saturated sodium bicarbonate aqueous solution was added thereto to make the mixture alkaline. The mixture was extracted with ethyl acetate, and then the aqueous layer was precipitated with 10% hydrochloric acid. The precipitated crystals were collected by filtration and washed with water to obtain 0.47 g (yield: 76%) of the desired compound.

Workup

  1. additionwas dropwise added
  2. stirringthe mixture was further stirred at room temperature for 4 hours
  3. concentrationIt was then concentrated under reduced pressure
  4. customto remove acetone
  5. additiona saturated sodium bicarbonate aqueous solution was added
  6. extractionThe mixture was extracted with ethyl acetate
  7. customthe aqueous layer was precipitated with 10% hydrochloric acid
  8. filtrationThe precipitated crystals were collected by filtration
  9. washwashed with water

Sources & evidence

ORD record
ord-f7bdde7295d34614a571b2a077a7bc7d
Source dataset
uspto-grants-1997_04
Patent number
US05616537

Reaction notes

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