Sodium Hydroxide → HCID 20489582, compound

HRID 1995093Notes

Reaction equation

HRID 1995093 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[CH:12][CH:11]=1)=O.O.NN.[OH-].[Na+]>C(O)COCCO.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 20489607HCID 20489607, compound

Product 1

HCID 20489582HCID 20489582, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8117Diethylene GlycolSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 15.8 g of 2-(2-pyridyl)-1-(4-quinolyl)-ethanone and 25 ml of 85% hydrazine hydrate in 250 ml of diethylene-glycol is heated at 160° C. for 30 minutes. After cooling to 60° C., 22 g of sodium hydroxide pellets are added and the mixture is heated at 160° C. for 2 hours. The reaction mixture is diluted with water, then extracted 3 times, each by 300 ml of methylene chloride. The organic phase is dried over magnesium sulfate and evaporated under reduced pressure. 12.5 g are thus obtained of 4-[-2-(2-pyridyl)-ethyl]-quinoline in the form of a lacquer. N.M.R. spectrum of the product obtained:

Workup

  1. temperatureAfter cooling to 60° C.
  2. temperaturethe mixture is heated at 160° C. for 2 hours
  3. extractionextracted 3 times
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-10e8d263f66a4237bfbad9a1ba01d769
Source dataset
uspto-grants-1983_09
Patent number
US04402961

Reaction notes

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