Ethanol → HCID 72743198, compound

HRID 1904664Notes

Reaction equation

HRID 1904664 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[CH2:7][CH2:8][N:9]2[C:12](=[O:21])[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])=[CH:4][CH:3]=1.C(O)C.Cl.[OH:27][NH2:28].N1C=CC=CC=1>O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[N:28][OH:27])[CH2:7][CH2:8][N:9]2[C:12](=[O:21])[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 10736881HCID 10736881, compound

Product 1

HCID 72743198HCID 72743198, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 7-chloro-1-(2,4-dichlorobenzo-yl)-2,3-dihydro-4(1H)-quinolinone (17.5 g), obtained in example 5, and ethanol (250 ml) were added hydroxyl amine hydrochloride (7 g) and pyridine (8.5 g), and the mixture was heated under reflux for 1.5 hours. After cooling, the reaction mixture was poured into 1000 ml of water, and precipitated crystals were separated by filtration, washed, dried and recrystallized with ethanol to obtain 7-chloro-1-(2,4-dichlorobenzoyl)-2,3-dihydro-4(1H)-quinolinone-4-oxime (yield 16 g) as white crystal.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureAfter cooling
  4. customprecipitated crystals
  5. customwere separated by filtration
  6. washwashed
  7. customdried
  8. customrecrystallized with ethanol

Sources & evidence

ORD record
ord-d6cccee9a3e54440977bf1451f42921a
Source dataset
uspto-grants-1989_06
Patent number
US04839368

Reaction notes

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