3-Cyanopyridine → HCID 178513339, compound

HRID 2249603Notes

Reaction equation

HRID 2249603 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].Cl.[NH2:10][OH:11].[Na]>CO>[OH:11][NH:10][C:1](=[NH:2])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1

Participants

5

Reactant 3

HCID 793-CyanopyridineHCID 443297Hydroxyamine hydrochlorideHCID 5360545Sodium

Product 1

HCID 178513339HCID 178513339, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Cyanopyridine (4.0 g) and hydroxylamine hydrochloride (3.2 g) were added to a solution of sodium (1.8 g) in MeOH (60 ml). The mixture was stirred 2.5 h at RT and refluxed 30 min. After cooling to RT, solids were filtered off. The solution was evaporated. White crystals (4.7 g) were obtained upon flash chromatography (125 g silica gel; CH2Cl2/MeOH 9:1) followed by a precipitation from heptan and ethyl acetate.

Workup

  1. temperaturerefluxed 30 min
  2. temperatureAfter cooling to RT
  3. filtrationsolids were filtered off
  4. customThe solution was evaporated

Sources & evidence

ORD record
ord-2027ae332d774006a52f4c31f59160bc
Source dataset
uspto-grants-2008_01
Patent number
US07314884B2

Reaction notes

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