Water → HCID 85729257, compound

HRID 613501Notes

Reaction equation

HRID 613501 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][C:8]=2[NH:14][C:15](=[O:24])[C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:23])(=O)[CH3:2].Cl.[NH2:26][OH:27].C(=O)(O)[O-].[Na+].O>C(O)C>[Cl:23][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=1[C:15]([NH:14][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[N:6]=[CH:5][C:4]([C:1](=[N:26][OH:27])[CH3:2])=[CH:13]2)=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 19592998HCID 19592998, compound

Product 1

HCID 85729257HCID 85729257, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-acetyl-8-(2,6-dichlorobenzoylamino)quinoline (399 mg), hydroxylamine hydrochloride (232 mg) and sodium bicarbonate (467 mg) in ethanol was refluxed for 5 hours. The mixture was poured into water and extracted with dichloromethane. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from ethanol to give 8-(2,6-dichlorobenzoylamino)-3-(1-hydroxyiminoethyl)quinoline (313 mg).

Workup

  1. temperaturewas refluxed for 5 hours
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-07819a6a17ec4291909fe0b49db95b19
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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