Potassium Permanganate → HCID 12898485, compound

HRID 1579393Notes

Reaction equation

HRID 1579393 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>[C:21]([C:19]1[CH:18]=[CH:17][C:15]2[O:16][C:8]3=[N:7][CH:12]=[CH:11][CH:10]=[C:9]3[C:13](=[O:2])[C:14]=2[CH:20]=1)(=[O:25])[CH:22]([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 21568412HCID 21568412, compound

Product 1

HCID 12898485HCID 12898485, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
20 °C

Procedure

11 g of potassium permanganate is added in small portions to a solution of 6 g of 1-(5H-[1]benzopyrano[2,3-b]pyridin-7-yl)-2-methyl-1 -propanol in 160 ml of acetone, and the mixture is stirred at 20°C for 3 hours. The reaction mixture is filtered, and the residue is washed thoroughly 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 acetone to give 7-isobutyryl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine melting at 155°-156°C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthe residue is washed thoroughly with chloroform
  3. concentrationThe filtrate and washings are concentrated
  4. customthe residue is purified by column chromatography on silica gel with chloroform as eluent
  5. customfurther by recrystallization from acetone

Sources & evidence

ORD record
ord-1f91f159dfe543b1ab0078d1a403e94a
Source dataset
uspto-grants-1976_01
Patent number
US03931199

Reaction notes

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