Hydrogen Peroxide → HCID 15044004, compound

HRID 1441116Notes

Reaction equation

HRID 1441116 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14](=[O:16])[CH2:13][CH:12]([Si](F)(C)C)[CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[F-].[K+].C(=O)(O)[O-:24].[Na+].OO>CO>[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14](=[O:16])[CH2:13][CH:12]([OH:24])[CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 516892Sodium BicarbonateHCID 522689Potassium FluorideHCID 15044003HCID 15044003, compound

Product 1

HCID 15044004HCID 15044004, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution 9-amino-3,4-dihydro-3-(fluorodimethylsilyl)acridin-1(2H)-one (3.7 g) 1:1-tetrahydrofuran:methanol (70 ml), potassium fluoride (7.45 g), and sodium bicarbonate (10.7 g) was chilled in an ice/water bath, and 30% aqueous hydrogen peroxide (44 ml) was added slowly. Upon completion of the addition, the bath was removed and stirring was continued for 3 hr. The reaction mixture was poured into water (250 ml) and a little diethyl ether was added. The mixture was filtered and the filter cake was washed with water and diethyl ether to give 2.6 g (89%) of product, mp 205° C. (dec).

Workup

  1. additionUpon completion of the addition
  2. customthe bath was removed
  3. additionThe reaction mixture was poured into water (250 ml)
  4. additiona little diethyl ether was added
  5. filtrationThe mixture was filtered
  6. washthe filter cake was washed with water and diethyl ether

Sources & evidence

ORD record
ord-15d52398697d4ea9aea6153fe6333d08
Source dataset
uspto-grants-1996_03
Patent number
US05502203

Reaction notes

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