O-methylhydroxylammonium chloride → 4-CHLORO-gamma-[1-(METHOXYIMINO)ETHYL]-beta-METHYLBENZENEBUTANENITRILE

HRID 1980336Notes

Reaction equation

HRID 1980336 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14](=O)[CH3:15])[CH:9]([CH3:13])[CH2:10][C:11]#[N:12])=[CH:4][CH:3]=1.[CH3:17][O:18][NH3+:19].[Cl-]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14](=[N:19][O:18][CH3:17])[CH3:15])[CH:9]([CH3:13])[CH2:10][C:11]#[N:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11639O-methylhydroxylammonium chlorideHCID 135028694-CHLORO-gamma-(1-OXOETHYL)-beta-METHYLBENZENEBUTANENITRILE

Product 1

HCID 540605114-CHLORO-gamma-[1-(METHOXYIMINO)ETHYL]-beta-METHYLBENZENEBUTANENITRILE

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

4-Chloro-γ-(1-oxoethyl)-β-methylbenzenebutanenitrile (4.4 grams) and methoxyamine.HCl (3.7 grams) in 80 ml of pyridine were stirred at ambient temperature. The mixture was then poured into ice containing sufficient concentrated HCl to neutralize the pyridine, stirred, and extracted with dichloromethane. The resulting dichloromethane solution was washed with water and a saturated solution of sodium chloride and was then dried over magnesium sulfate. Filtering and stripping resulted in a clear colorless gum which was shown by NMR and IR to be the desired product.

Workup

  1. additionThe mixture was then poured into ice containing sufficient concentrated HCl
  2. extractionextracted with dichloromethane
  3. washThe resulting dichloromethane solution was washed with water
  4. dry with materiala saturated solution of sodium chloride and was then dried over magnesium sulfate
  5. filtrationFiltering
  6. customstripping resulted in a clear colorless gum which

Sources & evidence

ORD record
ord-b93a490f7b0942d384552397ee46a0f3
Source dataset
uspto-grants-1985_04
Patent number
US04508722

Reaction notes

Loading…