Sodium ethoxide → HCID 89853500, compound

HRID 931125Notes

Reaction equation

HRID 931125 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[C:6]([C:10]#[N:11])[CH:5]=2)[CH2:3][CH2:2]1.[O-:12][CH2:13][CH3:14].[Na+]>C(O)C>[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[C:6]([C:10](=[NH:11])[O:12][CH2:13][CH3:14])[CH:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 753556264-cyclopropylpicolinonitrile

Product 1

HCID 89853500HCID 89853500, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-cyclopropylpicolinonitrile (0.04 g, 0.27 mmol) in ethanol was added sodium ethoxide (0.022 g, 0.33 mmol) and the reaction mixture was stirred at room temperature for 3 h. The reaction mixture was concentrated under vacuum, quenched with water, extracted with ethyl acetate, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford ethyl 4-cyclopropylpicolinimidate (0.045 g). The material was used without further purification. MS (ES+APCI) (M+H) 190.9; LCMS retention time 1.700 min (Method G).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d247faf44f4240a2b5d99dca8b15ec4c
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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