Hydrochloric Acid → Pyridine-2-aldoxime

HRID 1920906Notes

Reaction equation

HRID 1920906 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.Cl.[NH2:10][OH:11].[OH-].[Na+].Cl>C(O)C.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1/[CH:7]=[N:10]\[OH:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 142732-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 135564593Pyridine-2-aldoximeYield 78.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 2-pyridinecarboxaldehyde (53.6 g, 500 mmol) and hydroxylamine hydrochloride (38.2 g, 544 mmol) in ethanol (36 mL) and water (69 mL) was added ice (205 g). Then an aqueous solution of sodium hydroxide (32%, 115 mL, 1.24 mol) was added dropwise within a 10 min period (temperature rises from −8° C. to +7° C.) whereupon most of the solid dissolves. After 1 h stirring at room temperature the resulting mixture was then acidified with HCl (5 N). The mixture was then extracted with dichloromethane to afford the title compound (47.7 g, 78%) which was obtained as an off white solid. MS: m/e=123.3 [M+H]+.

Workup

  1. dissolutiondissolves
  2. extractionThe mixture was then extracted with dichloromethane

Sources & evidence

ORD record
ord-618a93f3368747ee989b14f9835141ea
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

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