Hydrochloric Acid → 2-(2-Phenoxyphenyl)-2-hydroxyiminoacetamide

HRID 1756754Notes

Reaction equation

HRID 1756754 reaction equation
[OH-:1].[K+].[O:3]([C:10]1[CH:20]=[CH:19][CH:18]=[CH:17][C:11]=1[C:12]([C:15]#[N:16])=[N:13][OH:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>C(O)(C)(C)C>[O:3]([C:10]1[CH:20]=[CH:19][CH:18]=[CH:17][C:11]=1[C:12](=[N:13][OH:14])[C:15]([NH2:16])=[O:1])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 853212152-Phenoxy-alpha-hydroxyiminobenzyl cyanide

Product 1

HCID 736779222-(2-Phenoxyphenyl)-2-hydroxyiminoacetamideYield 67.5%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

85% Potassium hydroxide (2.57 g, 38.9 mmol) and tert-butyl alcohol (40 ml) were added to 2-phenoxy-α-hydroxyiminobenzyl cyanide (E/Z=11/89)(3.10 g, 13 mmol). The mixture was heated under reflux for 10 hours. After completion of the reaction, the reaction mixture was neutralized with 1N hydrochloric acid, extracted with ethyl acetate (100 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting crystals were recrystallized from n-hexane/ethyl acetate to give 2-(2-phenoxyphenyl)-2-hydroxyiminoacetamide (2.25 g, Yield: 67.5%, Z=at least 98%) as pale yellow crystals.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 10 hours
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate (100 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting crystals were recrystallized from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-a24a73f67c0c4a67a6c9fc9f84827c1c
Source dataset
uspto-grants-1995_08
Patent number
US05442063

Reaction notes

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