Triethylamine → 1-[2-(6,7-Dimethoxy-quinolin-4-yloxy)-4,5-dimethyl-phenyl]-ethanone oxime

HRID 228729

Reaction equation

HRID 228729 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[C:20]([CH3:22])[C:19]([CH3:23])=[CH:18][C:17]=1[C:24](=O)[CH3:25].Cl.[NH2:28][OH:29].C(N(CC)CC)C>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[C:20]([CH3:22])[C:19]([CH3:23])=[CH:18][C:17]=1[C:24](=[N:28][OH:29])[CH3:25]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 443297Hydroxyamine hydrochloride2×HCID 100665381-(2-((6,7-Dimethoxyquinolin-4-yl)oxy)-4,5-dimethylphenyl)ethan-1-one2×

Product 1

HCID 866051871-[2-(6,7-Dimethoxy-quinolin-4-yloxy)-4,5-dimethyl-phenyl]-ethanone oximeYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[2-(6,7-Dimethoxy-quinolin-4-yloxy)-4,5-dimethylphenyl]-1-ethanone (compound 38) (30 mg) was dissolved in ethanol (1 ml) to prepare a solution. Hydroxylamine hydrochloride (12 mg) and triethylamine (27 mg) were added to the solution, and the mixture was stirred at room temperature overnight. Further, hydroxylamine hydrochloride (12 mg) and triethylamine (27 mg) were then added to the reaction solution, and the mixture was stirred at room temperature for 5 hr. The solvent was removed by distillation under the reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using hexane-acetone to give the title compound (10 mg, yield 31%).

Workup

  1. customto prepare a solution
  2. stirringthe mixture was stirred at room temperature for 5 hr
  3. customThe solvent was removed by distillation under the reduced pressure, water
  4. additionwas added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was then washed with water
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation under the reduced pressure
  9. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-b15d0aed05834478b77655be55040419
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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