HCID 54716313, compound → HCID 14368611, compound

HRID 1710072Notes

Reaction equation

HRID 1710072 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][C:24]([CH3:27])=[CH:23][N:22]=1)=[O:19]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:27][C:24]1[CH:25]=[CH:26][C:21]([NH:20][C:18]([C:3]2[C:2](=[O:1])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:4]=2)=[O:19])=[N:22][CH:23]=1

Participants

4

Reactant 1

HCID 54716313HCID 54716313, compound

Product 1

HCID 14368611HCID 14368611, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A solution of 12.30 g of 1,2-dihydro-4-hydroxy-N-(5-methyl-2-pyridyl)-1-phenyl-3-quinolinecarboxamide in 250 ml of chloroform was treated with 50.0 g of activated manganese dioxide and stirred at room temperature for two hours. The slurry was filtered and evaporated. Recrystallization of the residue from chloroform yielded 10.96 g (91%) of 1,4-dihydro-N-(5-methyl-2-pyridyl)-4-oxo-1-phenyl-3-quinolinecarboxamide, m.p. 248°-250° C.

Workup

  1. filtrationThe slurry was filtered
  2. customevaporated
  3. customRecrystallization of the residue from chloroform

Sources & evidence

ORD record
ord-b5bb7c9972554069a308a4ba039da3d4
Source dataset
uspto-grants-1990_08
Patent number
US04952588

Reaction notes

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