8-Chloro-5-(4-chlorophenyl)-5H-indeno[1,2-d]pyrimidine → 8-chloro-5-(4-chlorophenyl)-5H-indeno[1,2-d]pyrimidin-5-ol

HRID 622098Notes

Reaction equation

HRID 622098 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]2[C:5]([CH:6]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[C:7]3[CH:12]=[N:11][CH:10]=[N:9][C:8]=32)=[CH:4][CH:3]=1.[Mn]([O-])(=O)(=O)=[O:23].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)([OH:23])[C:7]3[CH:12]=[N:11][CH:10]=[N:9][C:8]=32)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1339698-Chloro-5-(4-chlorophenyl)-5H-indeno[1,2-d]pyrimidineHCID 516875Potassium Permanganate2×

Product 1

HCID 142570878-chloro-5-(4-chlorophenyl)-5H-indeno[1,2-d]pyrimidin-5-olYield 26.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 11.0 g of 8-chloro-5-(4-chlorophenyl)-5H-indeno[1,2-d]pyrimidine in 300 ml of acetone were added 6.32 g of potassium permanganate. The mixture was stirred under a nitrogen atmosphere for 2 hours at which time an additional 6.32 g of potassium permanganate were added. The mixture was stirred overnight at room temperature, filtered, and the filtrate concentrated in vacuo. The residue was taken up in a mixture of ethyl acetate and a saturated sodium chloride solution. The layers were separated and the organic layer was washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was crystallized first from ethyl acetate/isooctane and then from ethyl acetate to provide 3.06 g of the desired title product, m.p. 194°-195.5° C.

Workup

  1. additionwere added
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated in vacuo
  4. additionThe residue was taken up in a mixture of ethyl acetate
  5. customThe layers were separated
  6. washthe organic layer was washed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was crystallized first from ethyl acetate/isooctane

Sources & evidence

ORD record
ord-fabcc99b723a4f5498f80406b065329f
Source dataset
uspto-grants-1988_09
Patent number
US04769378

Reaction notes

Loading…