Hydroxyamine hydrochloride → HCID 54186551, compound

HRID 647561Notes

Reaction equation

HRID 647561 reaction equation
Cl.[NH2:2][OH:3].C(=O)(O)[O-].[K+].[CH2:9]([C:12]1[CH:24]=[CH:23][CH:22]=[CH:21][C:13]=1[O:14][CH2:15][CH:16]([OH:20])[CH2:17][C:18]#[N:19])[CH:10]=[CH2:11]>O.C(O)CCC>[NH2:2][OH:3].[CH2:9]([C:12]1[CH:24]=[CH:23][CH:22]=[CH:21][C:13]=1[O:14][CH2:15][CH:16]([OH:20])[CH2:17][C:18](=[N:2][OH:3])[NH2:19])[CH:10]=[CH2:11]

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516893Potassium BicarbonateHCID 13092564HCID 13092564, compound

Product 2

HCID 787HydroxylamineHCID 54186551HCID 54186551, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Conditions

Temperature
94 °C

Procedure

An aqueous solution of hydroxylamine is prepared from 39.06 g (0.562 mol) of hydroxylamine hydrochloride in 150 ml of water and from 56.2 g (0.562 mol) of potassium bicarbonate. 48.9 g (0.225 mol) of 4-(o-allylphenoxy)-3-hydroxy-butyronitrile previously dissolved in 250 ml of n-butanol are then added. The resulting mixture is taken to 80° C. in about 2 hours, then taken to reflux (94° C.) which is maintained for 5 hours. The mixture is cooled, the H2O--CH3 (CH2)2CH2OH mixture is evaporated, the residue of evaporation is taken up with ether, washed several times in water, dried and the ether is evaporated under reduced pressure. 48.5 g (yield 86%) of 4-(o-allyl-phenoxy)-3-hydroxy-butyramidoxime are obtained in the form of a brown oil.

Workup

  1. additionare then added
  2. temperatureis maintained for 5 hours
  3. temperatureThe mixture is cooled
  4. customthe H2O--CH3 (CH2)2CH2OH mixture is evaporated
  5. customthe residue of evaporation
  6. washwashed several times in water
  7. customdried
  8. customthe ether is evaporated under reduced pressure

Sources & evidence

ORD record
ord-6a8d6b930d8a4a289bc2418be4ae15d7
Source dataset
uspto-grants-1983_10
Patent number
US04409242

Reaction notes

Loading…