HCID 54716320, compound → HCID 14368605, compound

HRID 1089459Notes

Reaction equation

HRID 1089459 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][N:22]=1)=[O:19]>C1C=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][N:22]=1)=[O:19]

Participants

4

Reactant 1

HCID 54716320HCID 54716320, compound

Product 1

HCID 14368605HCID 14368605, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 241BenzeneSolvent

Procedure

A solution of 2.4 g of 1,2-dihydro-4-hydroxy-1-phenyl-N-(2-pyridyl)-3-quinolinecarboxamide in 150 ml of benzene was treated with 8.4 g of activated manganese dioxide. The slurry was stirred at room temperature for 30 minutes, filtered, and evaporated. Recrystallization of the residue from dichloromethane-diethyl ether afforded 2.19 g (92%) of 1,4-dihydro-4-oxo-1-phenyl-N-(2-pyridyl)-3-quinolinecarboxamide, m.p. 238°-240° C.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customRecrystallization of the residue from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-990985f5c0ff4868920829b48e499b4c
Source dataset
uspto-grants-1990_10
Patent number
US04966906

Reaction notes

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