Ethyl 1-cyanocyclopropanecarboxylate → Ethyl 1-(aminomethyl)cyclopropanecarboxylate

HRID 1485049Notes

Reaction equation

HRID 1485049 reaction equation
[C:1]([C:3]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4]1)#[N:2].[H][H]>C(O)C.[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 380810Ethyl 1-cyanocyclopropanecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 11480505Ethyl 1-(aminomethyl)cyclopropanecarboxylateYield 93%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution in ethanol (127 mL) of the compound (14.0 g) obtained in step (1) above, a Raney nickel catalyst (about 2.8 g) was added. In a hydrogen atmosphere, the mixture was stirred at room temperature for 12 hours and further stirred at 40° C. for 12 hours. After being cooled to room temperature, the reaction mixture was filtered through Celite (registered trademark) and the filtrate was concentrated under reduced pressure. The resulting precipitate was recovered by filtration and washed with ethanol. The filtrate was concentrated to give the titled compound as a red oil (13.4 g).

Workup

  1. temperatureAfter being cooled to room temperature
  2. filtrationthe reaction mixture was filtered through Celite (registered trademark)
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. filtrationThe resulting precipitate was recovered by filtration
  5. washwashed with ethanol
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f579ef5bccaa4fd8991178f7c4ffeccc
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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