Ammonia → Ethyl 1-(aminomethyl)cyclopropanecarboxylate

HRID 2361937Notes

Reaction equation

HRID 2361937 reaction equation
[C:1]([C:3]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4]1)#[N:2].N>C(O)C.O.[Ni]>[NH2:2][CH2:1][C:3]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 380810Ethyl 1-cyanocyclopropanecarboxylate

Product 1

HCID 11480505Ethyl 1-(aminomethyl)cyclopropanecarboxylateYield 67.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 19096565Water ethanolSolvent

Procedure

To a solution of ethyl 1-cyanocyclopropanecarboxylate (1 g, 7.18 mmol) in ethanol-water-conc. ammonia solution (7 ml-350 μl-1 ml) was added raney nickel (ca. 350 μl) and the mixture was sittred for 24 hr at 50° C. The reaction mixture was filtered through Celite and the filtrate was concentrated in vacuo to obtain the title compound (690 mg, 67%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2865bb43bd814960876c579e51ec530a
Source dataset
uspto-grants-2014_04
Patent number
US08691819B2

Reaction notes

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