3-Pyridinecarboxaldehyde → 2-Dimethoxymethyl-3-(3-pyridyl)acrylonitrile hydrate

HRID 496821Notes

Reaction equation

HRID 496821 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[O:8])[CH:2]=1.[CH3:9][O:10][CH:11]([O:15][CH3:16])[CH2:12][C:13]#[N:14].C[O-].[Na+]>CO>[OH2:8].[CH3:9][O:10][CH:11]([O:15][CH3:16])[C:12](=[CH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:13]#[N:14]

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 937313,3-DimethoxypropiononitrileHCID 10942334Sodium Methoxide

Product 1

HCID 697476732-Dimethoxymethyl-3-(3-pyridyl)acrylonitrile hydrateYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pyridine-3-carboxaldehyde (80.25 g, 0.75 mol) and 3,3-dimethoxypropionitrile (115.1 g, 1.0 mol) were mixed together and added to a solution of sodium methoxide (54.0 g, 1.0 mol) in methanol (400 mL) over a period of 15 minutes. The mixture was stirred at room temperature overnight. Most of the methanol was evaporated in vacuo and the residue was partitioned between ethyl acetate (500 mL) and water (450 mL). The organic layer was separated, washed with brine (400 mL), dried (MgSO4) and the solvent evaporated in vacuo. The residual oil was distilled in vacuo to give 80.3 g (52%) of the product as a colorless oil, bp 130-140° C. (2 mm Hg).

Workup

  1. customMost of the methanol was evaporated in vacuo
  2. customthe residue was partitioned between ethyl acetate (500 mL) and water (450 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (400 mL)
  5. dry with materialdried (MgSO4)
  6. customthe solvent evaporated in vacuo
  7. distillationThe residual oil was distilled in vacuo

Sources & evidence

ORD record
ord-37889746f0324195ae5068a4d81b7b2f
Source dataset
uspto-grants-2005_09
Patent number
US06946554B2

Reaction notes

Loading…