Ammonia → HCID 18999480, compound

HRID 274112Notes

Reaction equation

HRID 274112 reaction equation
O[N:2]=[C:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][CH:10]=1.N.[H][H]>C(O)C.[Ni].O>[NH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][CH:14]=1

Participants

7

Reactant 3

HCID 222AmmoniaHCID 73504073HCID 73504073, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18999480HCID 18999480, compoundYield 98.3%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In an autoclave, a solution of 75.1 g (0.27 mole) of ethyl 4-[(2-hydroxyiminocyclopentyl)methyl]benzeneacetate in 800 ml of anhydrous ethanol saturated with NH3 is combined with about 37.5 g of Raney Nickel in water. The mixture is stirred under 80 atmospheres of hydrogen, at 80° C. during 4 hours. After cooling, the catalyst is filtered and rinsed with ethanol. The concentrated filtrate under reduced pressure, gives 69.3 g (yield=98.3%) of an orange oil which crystallizes but which is used without any other purification.

Workup

  1. temperatureAfter cooling
  2. filtrationthe catalyst is filtered
  3. washrinsed with ethanol

Sources & evidence

ORD record
ord-d8880158563c471d87dad8a140d6d850
Source dataset
uspto-grants-1995_02
Patent number
US05387709

Reaction notes

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