Hydroxylamine → HCID 3683044, compound

HRID 1174489Notes

Reaction equation

HRID 1174489 reaction equation
[C:1]1([NH:7][CH2:8][CH2:9][C:10]#[N:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:12][OH:13]>CCO>[OH:13][N:12]=[C:10]([NH2:11])[CH2:9][CH2:8][NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 141003-Anilinopropionitrile

Product 1

HCID 3683044HCID 3683044, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(phenylamino)propanenitrile (1 g, 6.84 mmol) and NH2OH (50% in water, 0.63 cm3, 10.26 mmol) in EtOH (10 cm3) were heated to reflux for 24 hours, after which the solvent and excess hydroxylamine were removed by rotary evaporator. To the residue was added water (10 cm3) and the mixture was extracted with CH2Cl2 (100 cm3). The extracts were concentrated under reduced pressure and the residue was purified by column chromatography (silica, Et2O) to give N′-hydroxy-3-(phenylamino)propanimidamide (0.77 g, 62.8%) as a white solid, mp 93-95° C. (lit mp 91-91.5° C.).

Workup

  1. temperatureto reflux for 24 hours
  2. customafter which the solvent and excess hydroxylamine were removed by rotary evaporator
  3. additionTo the residue was added water (10 cm3)
  4. extractionthe mixture was extracted with CH2Cl2 (100 cm3)
  5. concentrationThe extracts were concentrated under reduced pressure
  6. customthe residue was purified by column chromatography (silica, Et2O)

Sources & evidence

ORD record
ord-9a1b16d1e3bc497c9b4cbc8c5db1f005
Source dataset
uspto-grants-2010_11
Patent number
US07838483B2

Reaction notes

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