Hydrochloric Acid → Pyridine-2-aldoxime

HRID 1695342Notes

Reaction equation

HRID 1695342 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[NH2:9][OH:10].[OH-].[Na+].Cl>C(O)C.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1/[CH:7]=[N:9]\[OH:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 142732-PyridinecarboxaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 135564593Pyridine-2-aldoximeYield 78.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a suspension of 2-pyridinecarboxaldehyde (47.8 mL, 500 mmol) and hydroxylamine (38.2 g, 550 mmol) in ethanol (37 mL) and water (111 mL) was added ice (213 g). Then a solution of sodium hydroxide (50 g, 1.25 mol) in water (51 mL) was added within a 30 min period (temperature rose from −8° C. to +10° 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 precipitate was then filtered off and dried 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. filtrationThe precipitate was then filtered off
  3. customdried

Sources & evidence

ORD record
ord-d10e4a5ca8614c20a6225894ba87c49e
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

Loading…