3,3-Dimethoxypropiononitrile → HCID 178495319, compound

HRID 1777386Notes

Reaction equation

HRID 1777386 reaction equation
Cl.[NH2:2][OH:3].C([O-])(O)=O.[Na+].[CH3:9][O:10][CH:11]([O:15][CH3:16])[CH2:12][C:13]#[N:14]>CO>[OH:3][NH:2][C:13](=[NH:14])[CH2:12][CH:11]([O:15][CH3:16])[O:10][CH3:9]

Participants

5

Reactant 3

HCID 937313,3-DimethoxypropiononitrileHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 178495319HCID 178495319, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of hydroxylamine monohydrochloride (3.2 g, 45.6 mmol) in MeOH (70 mL), NaHCO3 (3.8 g, 45.6 mmol) was added and stirred for 30 minutes at room temperature, and then a solution of 3,3-dimethoxypropanenitrile (5.0 g, 43.4 mmol) in MeOH (30 mL) was added dropwise thereto. The reaction mixture was stirred for 15 hours at 80° C. The mixture was allowed to cool to room temperature to filter off the salt produced, and the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography (HP-Sil 100 g, CHCl3/MeOH=99/1 to 90/10) to obtain the title compound (4.5 g) (pale yellow oil).

Workup

  1. stirringThe reaction mixture was stirred for 15 hours at 80° C
  2. temperatureto cool to room temperature
  3. filtrationto filter off the salt
  4. customproduced
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by column chromatography (HP-Sil 100 g, CHCl3/MeOH=99/1 to 90/10)

Sources & evidence

ORD record
ord-bfec9fa7ee054f258c42fc40d0319ebc
Source dataset
uspto-grants-2016_02
Patent number
US09266870B2

Reaction notes

Loading…