Sodium ethoxide → 3-Ethoxyisonicotinonitrile

HRID 1477747Notes

Reaction equation

HRID 1477747 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].Cl[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[C:12]#[N:13]>CN(C=O)C>[CH2:2]([O:1][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:11]=1[C:12]#[N:13])[CH3:3]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 106783063-Chloropyridine-4-carbonitrile

Product 1

HCID 128666953-Ethoxyisonicotinonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium ethoxide (53 mg, 0.74 mmol) was added to a 0° C. solution of 3-chloro-4-cyanopyridine (100 mg, 0.72 mmol) in DMF (1 mL). The mixture was stirred at 0° C. for 30 min and at rt for 2 h, then the mixture was concentrated in vacuo. To the residue Et2O was added, and the salts were filtered off. The filtrate was concentrated in vacuo to yield the title compound as a white solid. LC-MS A: tR=0.67 min; [M(35Cl)+H]+=149.06.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additionTo the residue Et2O was added
  3. filtrationthe salts were filtered off
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7d5c05e1d6704c8ca673b97cdd0a36fe
Source dataset
uspto-grants-2016_08
Patent number
US09403813B2

Reaction notes

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