HCID 54716335, compound → HCID 9967782, compound

HRID 1710068Notes

Reaction equation

HRID 1710068 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][C:3]=1[C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=[C:3]1[C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19]

Participants

4

Reactant 1

HCID 54716335HCID 54716335, compound

Product 1

HCID 9967782HCID 9967782, compoundYield 45.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 15.0 g of 1,2-dihydro-4-hydroxy-1-phenyl-N-phenyl-3-quinolinecarboxamide in 250 ml of toluene was treated with 60.0 g of activated manganese dioxide and stirred at room temperature for four hours. The slurry was filtered and evaporated. The residue was purified first by flash chromatography (silica gel: dichloromethane as eluent), and then by high pressure liquid chromatography (silica gel: dichloromethane). Recrystallization of the residue from dichloromethane yielded 6.75 g (45%) of 1,4-dihydro-4-oxo-1-phenyl-N-phenyl-3-quinolinecarboxamide, m.p. 203°-205° C.

Workup

  1. filtrationThe slurry was filtered
  2. customevaporated
  3. customThe residue was purified first by flash chromatography (silica gel: dichloromethane as eluent)
  4. customRecrystallization of the residue from dichloromethane

Sources & evidence

ORD record
ord-522f3dfd85424e54a984f296912b3dde
Source dataset
uspto-grants-1990_08
Patent number
US04952588

Reaction notes

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