Hydrochloric Acid → 3,5-Dichloro-4-pyridinecarbaldehyde oxime

HRID 1823284Notes

Reaction equation

HRID 1823284 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:10])[C:7]=1[CH:8]=O.Cl.[NH2:12][OH:13].[OH-].[Na+].Cl>C(OCC)C.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:12][OH:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 27629883,5-Dichloro-4-pyridinecarboxaldehyde

Product 1

HCID 1363488123,5-Dichloro-4-pyridinecarbaldehyde oximeYield 98.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 19096565Water ethanolSolvent

Procedure

Combine 3,5-dichloropyridine-4-carboxaldehyde (2.80 g, 0.016 mol) with hydroxylamine hydrochloride (1.13 g, 0.018 mol) and ice (50 g) in an ethanol/water (30 mL/30 mL) mixture. Add aqueous sodium hydroxide (1.63 g, 0.024 mol, in 20 mL of water) dropwise and stir for 4 h near ambient temperature. Adjust the mixture to approx. pH 7.0 with aqueous hydrochloric acid and extracte with diethyl ether. Dry the combined extracts over sodium sulfate and concentrate in vacuo to give the desired crude oxime (3.00 g, 88%) as a light solid. MS(ES): (M+1)+ 190.9, 192.9 m/z.

Workup

  1. dry with materialDry the combined extracts over sodium sulfate
  2. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-e0a1c12509244b5083ccc856b89e579c
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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