Sodium Hydroxide → 2-(6-Chloro-2-pyridinyl)-1-(3-methyl-2-furyl)ethanone oxime

HRID 1269064Notes

Reaction equation

HRID 1269064 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([C:11]2[O:12][CH:13]=[CH:14][C:15]=2[CH3:16])=O)[CH:5]=[CH:4][CH:3]=1.Cl.[NH2:18][OH:19].[OH-].[Na+]>CO>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([C:11]2[O:12][CH:13]=[CH:14][C:15]=2[CH3:16])=[N:18][OH:19])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 184466082-(6-Chloro-2-pyridinyl)-1-(3-methyl-2-furyl)ethanone

Product 1

HCID 858395372-(6-Chloro-2-pyridinyl)-1-(3-methyl-2-furyl)ethanone oximeYield 52.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(6-chloro-2-pyridinyl)-1-(3-methyl-2-furyl)ethanone (52.2 g, 221 mmol) in methanol (500 mL) was added hydroxylamine hydrochloride (76.96 g, 1.11 mol) followed by an aqueous solution of sodium hydroxide (44.3 g, 1.11 mol). The resultant suspension was heated at reflux for 2 hours and then cooled to room temperature. The mixture was concentrated and water was added to the residue while stirring. After stirring for 20 minutes, a white solid precipitated. This solid was collected by filtration and washed with water to give 2-(6-chloro-2-pyridinyl)-1-(3-methyl-2-furyl)ethanone oxime (29.0 g, 52%) as a white solid. 1H NMR (CDCl3): δ 7.54 (t, 1H), 7.31 (s, 1H), 7.15 (d, 1H), 7.10 (d, 1H), 6.28 (s, 1H), 4.34 (s, 2H), 2.22 (S 3H). MS m/z 273 (M+1).

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationThe mixture was concentrated
  3. additionwater was added to the residue
  4. stirringAfter stirring for 20 minutes
  5. customa white solid precipitated
  6. filtrationThis solid was collected by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-6906286ae029476d95463ad3998bbc4d
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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