Sodium Hydroxide → 1-(4-bromobenzyl)-5-(4-oxo-2-thioxothiazolidin-5-ylmethyl)-3,4-dihydro-1H-quinolin-2-one

HRID 504050Notes

Reaction equation

HRID 504050 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:16]3[C:11](=[C:12]([CH:17]=[C:18]4[S:22][C:21](=[S:23])[NH:20][C:19]4=[O:24])[CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9][C:8]2=[O:25])=[CH:4][CH:3]=1.[OH-].[Na+].CC(=NO)C(C)=NO.[BH4-].[Na+].S([O-])(O)(=O)=O.[K+]>CN(C=O)C.C1COCC1.O.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:16]3[C:11](=[C:12]([CH2:17][CH:18]4[S:22][C:21](=[S:23])[NH:20][C:19]4=[O:24])[CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9][C:8]2=[O:25])=[CH:26][CH:27]=1

Participants

10

Reactant 5

HCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 4311764Sodium borohydrideHCID 866139611-(4-bromobenzyl)-5-(4-oxo-2-thioxothiazolidine-5-ylidenemethyl)-3,4-dihydro-1H-quinolin-2-oneHCID 135459645Dimethylglyoxime

Product 1

HCID 866139601-(4-bromobenzyl)-5-(4-oxo-2-thioxothiazolidin-5-ylmethyl)-3,4-dihydro-1H-quinolin-2-oneYield 89%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

50 mg of 1-(4-bromobenzyl)-5-(4-oxo-2-thioxothiazolidine-5-ylidenemethyl)-3,4-dihydro-1H-quinolin-2-one was suspended in a mixed solvent of 0.15 ml of methanol, 0.1 ml of water, 0.08 ml of an aqueous 1 N-sodium hydroxide solution, and 0.1 ml of THF. 0.03 ml of a DMF (5 ml) solution of 42 mg of cobalt chloride 6-hydrate and 250 mg of dimethylglyoxime was further added to the suspension, and the mixture was heated to 30° C. to 40° C. An aqueous solution (0.1 ml) of 15 mg of sodium borohydride was added, followed by stirring for 30 minutes. A saturated aqueous potassium hydrogensulfate solution was added, the mixture was extracted with ethyl acetate, and the extract was washed with water. The extract was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by preparative silica gel thin layer chromatography (ethyl acetate:n-hexane=1:1) to give 44.7 mg (89% yield) of 1-(4-bromobenzyl)-5-(4-oxo-2-thioxothiazolidin-5-ylmethyl)-3,4-dihydro-1H-quinolin-2-one as a colorless amorphous solid, and further recrystallized from ethyl acetate-diethyl ether, giving a white powder.

Workup

  1. temperaturethe mixture was heated to 30° C. to 40° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe extract was washed with water
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by preparative silica gel thin layer chromatography (ethyl acetate:n-hexane=1:1)

Sources & evidence

ORD record
ord-9fe11b06a9954635aa8ede4473385d74
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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