Sodium Hydroxide → 3,5-Dichloro-4-pyridinecarbaldehyde oxime

HRID 2423418Notes

Reaction equation

HRID 2423418 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:10])[C:7]=1[CH:8]=O.[OH-:11].[Na+].Cl.[NH2:14]O>C(O)C.O>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:10])[C:7]=1[CH:8]=[N:14][OH:11]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 27629883,5-Dichloro-4-pyridinecarboxaldehyde

Product 1

HCID 1363488123,5-Dichloro-4-pyridinecarbaldehyde oximeYield 91%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 3,5-dichloro-4-pyridinecarbaldehyde (6.50 g, 36.9 mmol) in ethanol (55 mL) was added a solution of sodium hydroxide (1.77 g, 44.3 mmol) and hydroxylamine hydrochloride (3.08 g, 44.3 mmol) in water (30 mL). The suspension was heated to 90° C. The mixture was stirred at 90° C. for approximately 6.5 hours and then concentrated. Water was added and the resulting solid was isolated by filtration and dried under a nitrogen stream at 45° C. over phosphorus pentoxide to afford 3,5-dichloro-4-pyridinecarbaldehyde oxime (6.38 g, 33.4 mmol, 91%). 1H-NMR (400 MHz, DMSO-d6) δ 13.31 (s, 1H), 8.68 (s, 2H), 8.24 (s, 1H).

Workup

  1. concentrationconcentrated
  2. additionWater was added
  3. customthe resulting solid was isolated by filtration
  4. dry with materialdried under a nitrogen stream at 45° C. over phosphorus pentoxide

Sources & evidence

ORD record
ord-1c56a9c7478b49cf8b93b8246cc34708
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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