Ethanol → 6-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-one

HRID 1649246Notes

Reaction equation

HRID 1649246 reaction equation
Cl.[N+:2]([C:5]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:14][C:6]=1[CH:7]=[CH:8][C:9](OCC)=[O:10])([O-])=O.C(O)C.[OH-].[Na+]>[Ni].O>[N:18]1([C:15]2[CH:14]=[C:6]3[C:5](=[CH:17][CH:16]=2)[NH:2][C:9](=[O:10])[CH2:8][CH2:7]3)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 705346722-Nitro-5-piperazinylcinnamic acid ethyl ester hydrochloride

Product 1

HCID 111178966-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-oneYield 54.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 2-nitro-5-piperazinylcinnamate hydrochloride (3.5 g) was dissolved in a mixed solvent consisting of 150 ml of ethanol and 45 ml of water and the solution was adjusted to pH of about 7 with an aqueous sodium hydroxide. The solution was added 2 g of Raney nickel catalyst and placed in a glass autoclave followed by stirring at 80° C. under hydrogen gas pressure of 5 kg/cm2 for 4 hours. After removing hydrogen gas the reaction mixture was taken out and the catalyst was removed. The solution was concentrated to dryness and methanol was added to the residue to precipitate crystals, which then were collected by filtration and recrystallized from methanol to give 1.3 g of 6-(1-piperazinyl)-3,4-dihydrocarbostyril, m.p. 224°-231.5° C.

Workup

  1. customAfter removing hydrogen gas the reaction mixture
  2. customthe catalyst was removed
  3. concentrationThe solution was concentrated to dryness and methanol
  4. additionwas added to the residue
  5. customto precipitate crystals, which
  6. filtrationthen were collected by filtration
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-4a0ed36b73494479b7464c1071d00e34
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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