Sodium ethoxide → Ethyl 5-cyclopropylnicotinimidate

HRID 931138Notes

Reaction equation

HRID 931138 reaction equation
[CH:1]1([C:4]2[CH:5]=[N:6][CH:7]=[C:8]([CH:11]=2)[C:9]#[N:10])[CH2:3][CH2:2]1.[O-:12][CH2:13][CH3:14].[Na+]>C(O)C>[CH:1]1([C:4]2[CH:5]=[N:6][CH:7]=[C:8]([CH:11]=2)[C:9](=[NH:10])[O:12][CH2:13][CH3:14])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 574196235-Cyclopropylnicotinonitrile

Product 1

HCID 89853752Ethyl 5-cyclopropylnicotinimidateYield 76.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-cyclopropylnicotinonitrile (0.45 g, 3.1 mmol) in ethanol was added sodium ethoxide (0.212 g, 3.1 mmol). The reaction mixture was stirred at room temperature for 12 h. The solvent was removed under reduced pressure, and the residue was partitioned between water and ethyl acetate. The organic layer was concentrated under reduced pressure to afford the title compound (0.45 g) which was used without further purification. MS (ES+APCI) (M+H) 191.2; LCMS retention time 1.149 min (Method L1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between water and ethyl acetate
  3. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-03f382616c464bf09188db30f5a8de75
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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