Hydrochloric Acid → HCID 136359763, compound

HRID 1823289Notes

Reaction equation

HRID 1823289 reaction equation
[F:1][C:2]1[C:3]([CH:8]=O)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl.[NH2:11][OH:12].[OH-].[Na+].Cl>C(O)C.O>[F:1][C:2]1[C:3]([CH:8]=[N:11][OH:12])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 113440173-Fluoro-2-pyridinecarboxaldehyde

Product 1

HCID 136359763HCID 136359763, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Combine 3-fluoropyridine-2-carboxaldehyde (3.00 g, 0.024 mol) with hydroxylamine hydrochloride (1.70 g, 0.026 mol) and ice (50 g) in an ethanol/water (30 mL/30 mL) mixture. Add aqueous sodium hydroxide (2.46 g, 0.06 mol, in 25 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 extract with diethyl ether. Dry over sodium sulfate and concentrate in vacuo. Elute the resulting residue over silica gel using methanol/dichloromethane to give 2.59 g (77%) of the desired oxime as an off white solid. MS(ES): (M+1)+ 140.9, 142.0 m/z.

Workup

  1. extractionextract with diethyl ether
  2. dry with materialDry over sodium sulfate
  3. concentrationconcentrate in vacuo
  4. washElute the resulting residue over silica gel

Sources & evidence

ORD record
ord-e9722c53731647a6b8882711930f0a65
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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