Hydroxyamine hydrochloride → HCID 86614460, compound

HRID 1370165Notes

Reaction equation

HRID 1370165 reaction equation
C(=O)(O)[O-].[Na+].Cl.[NH2:7][OH:8].[CH2:9]([C:12]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:13]=1[CH:14]=O)[CH:10]=[CH2:11]>O.CO>[CH2:9]([C:12]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:13]=1[CH:14]=[N:7][OH:8])[CH:10]=[CH2:11]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 21933582HCID 21933582, compound

Product 1

HCID 86614460HCID 86614460, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

5.58 g of sodium bicarbonate were added to a solution of 4.62 g of hydroxylamine hydrochloride in 50 ml of water, and the mixture was cooled to 0° C. A solution of 9.7 g (44.32 mmol) of 2-allyl-6-chlorobenzaldehyde in 50 ml of methanol was added, and the mixture was stirred at room temperature overnight. The methanol was subsequently removed under reduced pressure and the residue was added with stirring to 300 ml of water. The aqueous phase was extracted with diethyl ether, the combined organic phases were washed with saturated ammonium chloride solution and dried and the solvent was removed. This gave 8.7 g (quantitative) of 2-allyl-6-chlorobenzaldehyde oxime in the form of a viscous oil.

Workup

  1. customThe methanol was subsequently removed under reduced pressure
  2. additionthe residue was added
  3. stirringwith stirring to 300 ml of water
  4. extractionThe aqueous phase was extracted with diethyl ether
  5. washthe combined organic phases were washed with saturated ammonium chloride solution
  6. customdried
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-3d09f31735c34b5c8d231c90a309cef6
Source dataset
uspto-grants-2003_06
Patent number
US06583089B1

Reaction notes

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