Triethylamine → {1-[2-(6,7-Dimethoxy-quinolin-4-yloxy)-4,5-dimethylphenyl]-ethylidene}-hydrazine

HRID 228727Notes

Reaction equation

HRID 228727 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].O.[NH2:28][NH2:29].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][NH2:29])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 100665381-(2-((6,7-Dimethoxyquinolin-4-yl)oxy)-4,5-dimethylphenyl)ethan-1-one2×

Product 1

HCID 74019351{1-[2-(6,7-Dimethoxy-quinolin-4-yloxy)-4,5-dimethylphenyl]-ethylidene}-hydrazineYield 69.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[2-(6,7-Dimethoxy-quinolin-4-yloxy)-4,5-dimethylphenyl]-1-ethanone (compound 38) (50 mg) was dissolved in ethanol (1.5 ml) to prepare a solution. Hydrazine monohydrate (20 mg) and triethylamine (45 mg) were added to the solution, and the mixture was stirred under reflux for 3 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. The residue was purified by thin layer chromatography using hexane-acetone to give the title compound (36 mg, yield 67%).

Workup

  1. customto prepare a solution
  2. temperatureunder reflux for 3 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-ce73a14adace4bf28a09af6d655a0cee
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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