HCID 19899069, compound → HCID 54297546, compound

HRID 1196664Notes

Reaction equation

HRID 1196664 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH2:13][CH2:14][CH2:15][CH:16]([C:18]([O:20][CH3:21])=[O:19])[CH2:17][C:11]=3[O:10][N:9]=2)=[CH:4][CH:3]=1>CO.[Ni]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH2:9])=[C:12]2[CH2:13][CH2:14][CH2:15][CH:16]([C:18]([O:20][CH3:21])=[O:19])[CH2:17][C:11]2=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 19899069HCID 19899069, compound

Product 1

HCID 54297546HCID 54297546, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

0.22 g of methyl 3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4H-cyclohept[d]isoxazole-7-carboxylate was dissolved in 12 ml of methanol, 0.19 g of wet Raney-nickel was added and the mixture was hydrogenolyzed at 3.4 atmospheres and at room temperature for 30 hours. The catalyst was removed by filtration and washed on the filter firstly with ethanol and then with dichloromethane. The filtrate was evaporated and the residue was purified by chromatography on silica gel using ethyl acetate for the elution. There was obtained 0.155 g of methyl 4-[(4-chlorophenyl)(amino)methylene]-3-oxocycloheptanecarboxylate of melting point 154°-155° C.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed on the
  3. filtrationfilter firstly with ethanol
  4. customThe filtrate was evaporated
  5. customthe residue was purified by chromatography on silica gel
  6. washfor the elution

Sources & evidence

ORD record
ord-39488944b75a46b2911d9fa348d6e0f6
Source dataset
uspto-grants-1992_05
Patent number
US05114960

Reaction notes

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