Hydrogen Peroxide → HCID 9818249, compound

HRID 1585574Notes

Reaction equation

HRID 1585574 reaction equation
[C:1]([N:9]1[C:18]2[C:13](=[CH:14][C:15]([Cl:19])=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]1[C:20]#[N:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-:23].[Na+].[OH-].[Na+].OO>CC(C)=O.C(OCC)(=O)C>[C:1]([N:9]1[C:18]2[C:13](=[CH:14][C:15]([Cl:19])=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]1[C:20]([NH2:21])=[O:23])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium Hydroxide2×HCID 516892Sodium BicarbonateHCID 133367791-Benzoyl-6-chloro-1,2-dihydroquinoline-2-carbonitrile

Product 1

HCID 9818249HCID 9818249, compoundYield 17.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(Benzoyl)-6-chloro-1,2-dihydro-quinoline-2-carbonitrile (8.0 g), sodium bicarbonate (4.0 g), and 0.1N aqueous sodium hydroxide (20 mL) in acetone (125 mL) was treated with slow addition of 30% hydrogen peroxide (120 mL). The pH of the reaction was kept near 8 by the addition of 0.1N sodium hydroxide. After 4 hours, the mixture was diluted with ethyl acetate and washed with an aqueous solution of sodium thiosulfate. The organic phase was subsequently washed with water and brine. The organic phase was dried over magnesium sulfate and evaporated to dryness. The residue was chromatographed on silica gel using ethyl acetate/hexane (2:8) followed by ethyl acetate/methylene chloride/hexane (3:1:6) and finally 100% ethyl acetate to yield 1.5 g of the desired compound as a white solid, m.p. 230-234° C.

Workup

  1. washwashed with an aqueous solution of sodium thiosulfate
  2. washThe organic phase was subsequently washed with water and brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-4d61af87df2542f0b74f31d4919441e7
Source dataset
uspto-grants-1999_08
Patent number
US05939435

Reaction notes

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