Hydroxyamine hydrochloride → 4,6-Dichloro-5-pyrimidinecarbaldehyde oxime

HRID 405978

Reaction equation

HRID 405978 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=O)=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1.CC([O-])=O.[Na+].[NH2:16][OH:17].Cl>CCO>[Cl:1][C:2]1[C:7]([CH:8]=[N:16][OH:17])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 8196914,6-Dichloro-5-pyrimidinecarbaldehyde

Product 1

HCID 760165164,6-Dichloro-5-pyrimidinecarbaldehyde oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4,6-dichloropyrimidine-5-carbaldehyde (8.00 g, 44.8 mmol), NaOAc (3.7 g, 1.0 eq) and NH2OH.HCl (3.1 g, 1.0 eq) in EtOH (320 mL) was stirred at rt for 2 h. The reaction mixture was filtered, concd and purified by column chromatography on silica gel (dry loading, first DCM then DCM/EtOAc, 1/9) to give 4,6-dichloropyrimidine-5-carbaldehyde oxime as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customconcd and purified by column chromatography on silica gel (
  3. dry with materialdry loading, first DCM

Sources & evidence

ORD record
ord-afbae19d534f4d49a5b77e55dbfc9687
Source dataset
uspto-grants-2014_06
Patent number
US08754089B2

Linked notes

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