Ammonia → Ethyl 4-(2-aminoethyl)-2-chlorobenzoate

HRID 411759Notes

Reaction equation

HRID 411759 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([CH2:13][C:14]#[N:15])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].N.[H][H]>[Ni].CO>[NH2:15][CH2:14][CH2:13][C:11]1[CH:10]=[CH:9][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]([Cl:1])[CH:12]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 18541412Ethyl 2-chloro-4-(cyanomethyl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 18541437Ethyl 4-(2-aminoethyl)-2-chlorobenzoateYield 77%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture composed of 1.9 g (8.5 mmol) of ethyl 2-chloro-4-(cyanomethyl)benzoate, 0.5 g of Raney nickel in 70 ml of methanol containing a few ml of liquid ammonia is subjected to a hydrogen pressure of about 60 kg/cm2, at 50° C. for 5 h, and then at 80° C. for 4.5 h. After filtration of the reaction medium, 1.5 g of oil are obtained (Yield=77%).

Workup

  1. filtrationAfter filtration of the reaction medium, 1.5 g of oil
  2. customare obtained (Yield=77%)

Sources & evidence

ORD record
ord-aa5eca3213f745fbb36d4389940e802e
Source dataset
uspto-grants-2003_05
Patent number
US06559185B2

Reaction notes

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