Water → 8-(2,6-Dichlorobenzoylamino)-3-hydroxymethylquinoline

HRID 613485Notes

Reaction equation

HRID 613485 reaction equation
C([O:4][CH2:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[NH:16][C:17](=[O:26])[C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:25])(=O)C.[OH-].[Na+].O>O1CCOCC1.CN(C)C=O>[Cl:25][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([Cl:24])[C:18]=1[C:17]([NH:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[N:8]=[CH:7][C:6]([CH2:5][OH:4])=[CH:15]2)=[O:26]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 195927753-Acetoxymethyl-8-(2,6-dichlorobenzoylamino)quinoline

Product 1

HCID 195922958-(2,6-Dichlorobenzoylamino)-3-hydroxymethylquinolineYield 86.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-acetoxymethyl-8-(2,6-dichlorobenzoylamino)quinoline (25.9 mg), 1N sodium hydroxide solution (0.24 ml) in dioxane and dimethylformamide (4 drops) was stirred for 2 hours at ambient temperature. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from ethyl acetate-n-hexane to give 8-(2,6-dichlorobenzoylamino)-3-hydroxymethylquinoline (20 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 recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-59c3adddf5d241c29175a9b440531623
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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