Hydrochloric Acid → 2-Chloropyridine-3-carboxaldehyde oxime

HRID 1823263Notes

Reaction equation

HRID 1823263 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=O)=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[NH2:11][OH:12].[OH-].[Na+].Cl>C(O)C.O>[Cl:1][C:2]1[C:7]([CH:8]=[N:11][OH:12])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 7376072-Chloro-3-pyridinecarboxaldehyde

Product 1

HCID 27634542-Chloropyridine-3-carboxaldehyde oximeYield 91.1%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Combine 2-chloropyridine-3-carboxaldehyde (2.75 g, 0.0195 mol) with hydroxylamine hydrochloride (1.38 g, 0.021 mol) and ice (40 g) in an ethanol/water (15 mL/15 mL) mixture. Add aqueous sodium hydroxide (1.95 g, 0.049 mol, in 5 mL of water) dropwise and stir for 2.5 h near ambient temperature. Adjust the mixture to approx. pH 7.0 with aqueous hydrochloric acid, allowing for product precipitation. Extract with diethyl ether and wash with water and dry over sodium sulfate. Concentrate to obtain the desired crude oxime (2.78 g, 91%) as a white solid. MS(EI): (M)+ 156.3, 158.3 m/z.

Workup

  1. customallowing for product precipitation
  2. extractionExtract with diethyl ether
  3. washwash with water
  4. dry with materialdry over sodium sulfate
  5. concentrationConcentrate

Sources & evidence

ORD record
ord-b6d96089485d48ce907631b45467d6ff
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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