Ethanol → HCID 85551122, compound

HRID 1904662Notes

Reaction equation

HRID 1904662 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:20])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])=[CH:4][CH:3]=1.C(O)C.Cl.[OH:26][NH2:27].N1C=CC=CC=1>O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[N:27][OH:26])[CH2:7][CH2:8][N:9]2[C:12](=[O:20])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 10566097HCID 10566097, compound

Product 1

HCID 85551122HCID 85551122, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 7-chloro-2,3-dihydro-1-(2-methylbenzoyl)-4-(1H)-quinolinone (14.9 g), obtained in example 1, 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-2,3-dihydro-1-(2-methylbenzoyl)-4(1H)-quinolinone-4-oxime (yield 13.6 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-750b7cc9061c4132bca3f9f1337ee088
Source dataset
uspto-grants-1989_06
Patent number
US04839368

Reaction notes

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