Hydrochloric Acid → HCID 57365610, compound

HRID 1823276Notes

Reaction equation

HRID 1823276 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]=O.Cl.[NH2:11][OH:12].[OH-].[Na+].Cl>C(O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]=[N:11][OH:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 140466744-Chloropyridine-3-carbaldehyde

Product 1

HCID 57365610HCID 57365610, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Combine 4-chloropyridine-3-carboxaldehyde (2.75 g, 0.020 mol) with hydroxylamine hydrochloride (1.38 g, 0.021 mol) and ice (50 g) in an ethanol/water (25 mL/25 mL) mixture. Add aqueous sodium hydroxide (2.00 g, 0.049 mol, in 25 mL of water) dropwise and stir for 3 h near ambient temperature. Adjust the mixture to approx. pH 7.0 with aqueous hydrochloric acid and extract with diethyl ether. Dry the combined extracts over sodium sulfate and concentrate in vacuo which leaves the desired crude oxime (2.67 g, 88%). MS(ES): (M+1)+ 156.0, 158.0 m/z.

Workup

  1. extractionextract with diethyl ether
  2. dry with materialDry the combined extracts over sodium sulfate
  3. concentrationconcentrate in vacuo which

Sources & evidence

ORD record
ord-e85369ced70148d2b2bda9a39873d10a
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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