HCID 54716323, compound → HCID 14368612, compound

HRID 1089466Notes

Reaction equation

HRID 1089466 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH2:14][N:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:16]2[C:21]([C:22]=1[OH:23])=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:12]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:14]=1)=[O:12]

Participants

4

Reactant 1

HCID 54716323HCID 54716323, compound

Product 1

HCID 14368612HCID 14368612, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 9.66 g of N-(2-benzothiazolyl)-1,2-dihydro-4-hydroxy-1-phenyl-3-quinolinecarboxamide in 250 ml of toluene was treated with 39.0 g of activated manganese dioxide and stirred for four hours at room temperature. The slurry was filtered and evaporated. The residue was purified by means of high pressure liquid chromatography (silica gel: dichloromethane as the eluent) followed by recrystallization from dichloromethane to yield 4.6 g (48%) of N-(2-benzothiazolyl)-1,4-dihydro-4-oxo-1-phenyl-3-quinolinecarboxamide, m.p. 295°-297° C.

Workup

  1. filtrationThe slurry was filtered
  2. customevaporated
  3. customThe residue was purified by means of high pressure liquid chromatography (silica gel
  4. customdichloromethane as the eluent) followed by recrystallization from dichloromethane

Sources & evidence

ORD record
ord-5ca40ad7249147cd958c578792719c1f
Source dataset
uspto-grants-1990_10
Patent number
US04966906

Reaction notes

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