HCID 54716318, compound → HCID 14368609, compound

HRID 2232112Notes

Reaction equation

HRID 2232112 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[S:22][CH:23]=[C:24]([CH3:26])[N:25]=1)=[O:19]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH3:26][C:24]1[N:25]=[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])[S:22][CH:23]=1

Participants

4

Reactant 1

HCID 54716318HCID 54716318, compound

Product 1

HCID 14368609HCID 14368609, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 9.0 g of 1,2-dihydro-4-hydroxy-N-(4-methyl-2-thiazolyl)-1-phenyl-3-quinolinecarboxamide in 250 ml of hot toluene was treated with 36.0 g of activated manganese dioxide and stirred for two hours at ambient temperature. The slurry was filtered and evaporated. Recrystallization of the residue from chloroform yielded 6.0 g (66%) of 1,4-dihydro-N-(4-methyl-2-thiazolyl)-4-oxo-1-phenyl-3-quinolinecarboxamide, m.p. 252°-254° C.

Workup

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

Sources & evidence

ORD record
ord-331ac7ca3a7a4b4fba8b58c8386e6673
Source dataset
uspto-grants-1988_11
Patent number
US04786644

Reaction notes

Loading…