Hydroxylamine → HCID 178510888, compound

HRID 2169231Notes

Reaction equation

HRID 2169231 reaction equation
[C:1]1([C:7]2[C:8]([CH2:13][C:14]#[N:15])=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:16][OH:17].C(OCC)(=O)C>C(O)C.CCCCCC>[OH:17][NH:16][C:14](=[NH:15])[CH2:13][C:8]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 8857Ethyl AcetateHCID 537361012-(3-Phenylpyridin-2-yl)acetonitrile

Product 1

HCID 178510888HCID 178510888, compoundYield 92.33%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of (3-phenyl-pyridin-2-yl)-acetonitrile (159) (4.9 g, 25.26 mmol) in ethanol (250 mL) was added 50% aqueous NH2OH (3.4 mL, 50.51 mmol) and the mixture was heated at 60° C. for 16 h. Silica thin layer chromatography was performed (40% ethyl acetate in hexane, Rf=0.2). Ethanol was evaporated, water (50 mL) was added, the mixture was extracted with etylacetate (3×50 mL), dried and concentrated to get N-hydroxy-2-(3-phenyl-pyridin-2-yl)-acetamidine (160) (5.3 g, 92.33%, crude) as a yellow solid.

Workup

  1. customEthanol was evaporated
  2. additionwater (50 mL) was added
  3. extractionthe mixture was extracted with etylacetate (3×50 mL)
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3c29114dec274fefb234c0d283d2a35e
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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