Sodium Carbonate → 2-amino-N'-hydroxypyridine-4-carboximidamide

HRID 1989135Notes

Reaction equation

HRID 1989135 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.Cl.[NH2:11][OH:12].C(=O)([O-])[O-].[Na+].[Na+]>O.C(O)C>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([NH:11][OH:12])=[NH:9])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 70155242-Aminoisonicotinonitrile

Product 1

HCID 1785133752-amino-N'-hydroxypyridine-4-carboximidamideYield 68.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A stirred mixture of commercially available 2-amino-4-cyano-pyridine [CAS-No. 42182-27-4] (1.0 g, 8.39 mmol), hydroxylamine hydrochloride (1.17 g, 16.8 mmol) and sodium carbonate (0.89 g, 8.39 mol) in water (8 mL) and ethanol (16 mL) was heated under reflux conditions for 3 h. The reaction mixture was evaporated, water (10 mL) was added and the mixture stirred at room temperature for 1 h. The precipitate was collected by filtration to yield the title compound (0.87 g, 68%) as an off-white solid. MS (EI) 152.0 [(M)+]; mp 188° C.

Workup

  1. temperaturewas heated under reflux conditions for 3 h
  2. customThe reaction mixture was evaporated
  3. additionwater (10 mL) was added
  4. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-3f66b59164b3445e8c039f853b146a26
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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