HCID 58416506, compound → HCID 58416509, compound

HRID 1014996Notes

Reaction equation

HRID 1014996 reaction equation
[CH3:1][C:2]1([C:7]2[C:8]([CH2:13][C:14]#[N:15])=[N:9][CH:10]=[CH:11][CH:12]=2)[O:6][CH2:5][CH2:4][O:3]1>C(O)C.[Ni]>[CH3:1][C:2]1([C:7]2[C:8]([CH2:13][CH2:14][NH2:15])=[N:9][CH:10]=[CH:11][CH:12]=2)[O:3][CH2:4][CH2:5][O:6]1

Participants

4

Reactant 1

HCID 58416506HCID 58416506, compound

Product 1

HCID 58416509HCID 58416509, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

[3-(2-Methyl-1,3-dioxolan-2-yl)-2-pyridyl]methyl cyanide (540 mg, 2.64 mmol, 1.0 equiv) is dissolved in ethanol. A catalytic amount of Raney Nickel is added and the resulting mixture is placed under a hydrogen atmosphere. The mixture is stirred for 7 h using a hot water bath to warm the reaction mixture. After flushing with nitrogen, the mixture is filtered over kieselguhr and rinsed with ethyl acetate. The filtrate is concentrated in vacuo with replenishment of dichloromethane. This gave 490 mg of the title compound as a yellow oil.

Workup

  1. temperatureto warm the reaction mixture
  2. customAfter flushing with nitrogen
  3. filtrationthe mixture is filtered over kieselguhr
  4. washrinsed with ethyl acetate
  5. concentrationThe filtrate is concentrated in vacuo with replenishment of dichloromethane

Sources & evidence

ORD record
ord-94e07edd28694984915945f4e3dfb648
Source dataset
uspto-grants-2011_07
Patent number
US07985753B2

Reaction notes

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