Ethanol → HCID 86744332, compound

HRID 1073065Notes

Reaction equation

HRID 1073065 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]([C:14]2[CH:18]=[CH:17][S:16][C:15]=2[CH3:19])=[O:13])=[CH:4][CH:3]=1.C(O)C.Cl.[OH:25][NH2:26].N1C=CC=CC=1>O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[N:26][OH:25])[CH2:7][CH2:8][N:9]2[C:12]([C:14]2[CH:18]=[CH:17][S:16][C:15]=2[CH3:19])=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 23054596HCID 23054596, compound

Product 1

HCID 86744332HCID 86744332, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 7-chloro-2,3-dihydro-l-(2-methyl-3-thienylcarbonyl)-4(lH)-quinolinone (17.5 g), obtained in example 5, and ethanol (250 ml) were added hydroxyl amine hydrochloride (8 g) and pyridine (8.8 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-methyl-3-thienylcarbonyl)-4(lH)-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-cb0d0b2b06064c4882c049d39fe1dd8c
Source dataset
uspto-grants-1990_11
Patent number
US04968680

Reaction notes

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