Sodium Hydroxide → HCID 22643417, compound

HRID 2414785Notes

Reaction equation

HRID 2414785 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[N:12](C(C)=C)[C:11]2[CH:16]=[CH:17][CH:18]=[CH:19][C:10]=2[N:9]=1.[O-][Mn](=O)(=O)=O.[K+].[OH-].[Na+]>CC(O)(C)C>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[NH:12][C:11]2[CH:16]=[CH:17][CH:18]=[CH:19][C:10]=2[N:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 22643420HCID 22643420, compound

Product 1

HCID 22643417HCID 22643417, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

1.2 g of the compound obtained in Example 13b was dissolved in 10 ml of tBuOH, slowly added dropwise with 30 ml of a mixed solution of KMnO4; (1.92 g) and 50 ml of 0.1 N NaOH, and stirred for 1 hour. The reaction mixture was extracted three times with chloroform. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (ethyl acetate) to obtain 0.45 g of the title compound (yield: 43%).

Workup

  1. extractionThe reaction mixture was extracted three times with chloroform
  2. customThe solvent was evaporated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-fc6fdeffe45c4c1bb4bb3b9f98f3674b
Source dataset
uspto-grants-2004_11
Patent number
US06815455B1

Reaction notes

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