Ethyl Acetate → HCID 22902332, compound

HRID 1489665Notes

Reaction equation

HRID 1489665 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[N:23]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=3)[O:21][N:20]=2)[CH3:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[NH3+]N.C(OCC)(=O)C>C(O)C.[Ni]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[N:23]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=3)[O:21][N:20]=2)[CH3:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 22902362HCID 22902362, compoundHCID 44558531Aminoammonium hydroxide

Product 1

HCID 22902332HCID 22902332, compoundYield 23.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

5 g of 3-{3-[N-(2-(3,4-dimethoxyphenyl)-ethyl)-N-methylamino]-propyloxy}-5-(4-nitrophenyl)-1,2,4-oxadiazole (for preparation, see Example 67) were dissolved in 500 ml ethanol. 4 ml of hydrazinium hydroxide and a catalytic quantity of Raney nickel were added to the solution and the reaction mixture was heated at 50° C. for 30 minutes. The catalyst was then filtered off and the filtrate was concentrated to dryness. The remaining residue was reacted with 10% aqueous sodium carbonate solution and shaken with ethyl acetate. The organic phase was dried with sodium sulfate, filtered, and concentrated. The crude oily title compound that remained as a residue was purified by medium-pressure chromatography over silica gel (Lichroprep Si 60®) using 99:1 ethyl acetate/methanol as the eluent. 1.1 g of the title compound were obtained as an oil.

Workup

  1. filtrationThe catalyst was then filtered off
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe remaining residue was reacted with 10% aqueous sodium carbonate solution
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customwas purified by medium-pressure chromatography over silica gel (Lichroprep Si 60®)

Sources & evidence

ORD record
ord-d66271aec887446888b7f616422509ef
Source dataset
uspto-grants-1997_10
Patent number
US05679699

Reaction notes

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