Water → HCID 19592343, compound

HRID 613506Notes

Reaction equation

HRID 613506 reaction equation
Br[CH2:2][C:3]1[C:12]2[C:7](=[C:8]([NH:13][C:14](=[O:23])[C:15]3[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:22])[CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]=1[C:24]#[N:25].[C:26]([O-:29])(=[O:28])[CH3:27].[Na+].O>CN(C)C=O>[C:26]([O:29][CH2:2][C:3]1[C:12]2[C:7](=[C:8]([NH:13][C:14](=[O:23])[C:15]3[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:22])[CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]=1[C:24]#[N:25])(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 962WaterHCID 517045Sodium AcetateHCID 19592371HCID 19592371, compound

Product 1

HCID 19592343HCID 19592343, compoundYield 23.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-bromomethyl-8-(2,6-dichlorobenzoylamino)-3-cyanoquinoline (238 mg) and sodium acetate (94 mg) in dimethylformamide (1 ml) was stirred at ambient temperature overnight. To the residue was added water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (n-hexane-dichloromethane) to give 4-acetoxymethyl-3-cyano-8-(2,6-dichlorobenzoylamino)quinoline (54 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography (n-hexane-dichloromethane)

Sources & evidence

ORD record
ord-ba4a5878ec044bffa99f86470af43a4b
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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