Potassium Permanganate → HCID 13207925, compound

HRID 1579381Notes

Reaction equation

HRID 1579381 reaction equation
[Mn]([O-])(=O)(=O)=[O:2].[K+].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]2[CH2:13][C:14]3[CH:20]=[C:19]([CH:21]([OH:25])[CH:22]([CH3:24])[CH3:23])[CH:18]=[CH:17][C:15]=3[O:16][C:8]=12>CC(C)=O>[O:2]=[C:13]1[C:9]2[C:8](=[N:7][CH:12]=[CH:11][CH:10]=2)[O:16][C:15]2[CH:17]=[CH:18][C:19]([CH:21]([OH:25])[CH:22]([CH3:23])[CH3:24])=[CH:20][C:14]1=2

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 21568412HCID 21568412, compound

Product 1

HCID 13207925HCID 13207925, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

15 g of potassium permanganate is added in small portions to a solution of 11 g of 1(5H-[1]benzopyrano[2,3-b]pyridin-7-yl)-2-methyl-1-propanol in 200 ml of acetone, while the temperature is kept at 10°C. Then the mixture is allowed to stand at 20°C for 1 hour. The reaction mixture is filtered, and the crystalline residue is washed with chloroform. The filtrate and washings are concentrated, and the residue is purified by column chromatography on silica gel with chloroform as eluent, and further by recrystallization from ethanol to give 1-(5-oxo-5H-[1]-benzopyrano[2,3-b]-pyridin-7-yl)-2-methyl-1-propanol melting at 160°C.

Workup

  1. customis kept at 10°C
  2. filtrationThe reaction mixture is filtered
  3. washthe crystalline residue is washed with chloroform
  4. concentrationThe filtrate and washings are concentrated
  5. customthe residue is purified by column chromatography on silica gel with chloroform as eluent
  6. customfurther by recrystallization from ethanol

Sources & evidence

ORD record
ord-910602d8487145259a524909548a6065
Source dataset
uspto-grants-1976_01
Patent number
US03931199

Reaction notes

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