Potassium Permanganate → HCID 15239997, compound

HRID 1653648Notes

Reaction equation

HRID 1653648 reaction equation
[C:1]([NH:4][C:5]1[N:10]=[C:9]([CH:11]=[O:12])[C:8]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Mn]([O-])(=O)(=O)=[O:22].[K+]>CC(C)=O>[C:1]([NH:4][C:5]1[N:10]=[C:9]([C:11]([OH:22])=[O:12])[C:8]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 15239996HCID 15239996, compound

Product 1

HCID 15239997HCID 15239997, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4.9 g (18 mmol) of 6-acetylamino-3-benzyloxypicoline aldehyde was added to 100 ml of acetone. 400 ml of an aqueous solution of 4.3 g (27 mmol) of potassium permanganate was added thereto, and the mixture was stirred at room temperature for one hour. Precipitated manganese dioxide was filtered off and washed with 100 ml of hot water. The filtrate was extracted with ethyl acetate, and the aqueous layer was neutralized with citric acid. Precipitated crystals were extracted with chloroform, washed with water, dried and concentrated. The crystals thereby obtained were washed with diisopropyl ether to obtain 6-acetylamino-3-benzyloxy picolinic acid.

Workup

  1. filtrationPrecipitated manganese dioxide was filtered off
  2. washwashed with 100 ml of hot water
  3. extractionThe filtrate was extracted with ethyl acetate
  4. customPrecipitated crystals
  5. extractionwere extracted with chloroform
  6. washwashed with water
  7. customdried
  8. concentrationconcentrated
  9. customThe crystals thereby obtained
  10. washwere washed with diisopropyl ether

Sources & evidence

ORD record
ord-a89f8ca4fb9c4276ba2df0011ef9e967
Source dataset
uspto-grants-1995_04
Patent number
US05403816

Reaction notes

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