Methanol → 2-(2,5-Dimethylphenoxymethyl)-alpha-methoxyiminophenylacetohydrazide

HRID 1004362Notes

Reaction equation

HRID 1004362 reaction equation
CO.C1COCC1.O.[NH2:9][NH2:10].[CH3:11][C:12]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][C:13]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](=[N:27][O:28][CH3:29])[C:23](OC)=[O:24]>O>[CH3:11][C:12]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][C:13]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](=[N:27][O:28][CH3:29])[C:23]([NH:9][NH2:10])=[O:24]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 54440278Methyl 2-(2,5-dimethylphenoxymethyl)-alpha-methoxyiminophenylacetate

Product 1

HCID 865846752-(2,5-Dimethylphenoxymethyl)-alpha-methoxyiminophenylacetohydrazideYield 89.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methanol (10 ml), THF (10 ml) and hydrazine monohydrate (1.68 g, 0.03 mol) were added to methyl 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetate (3.27 g, 0.01 mol), and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, water (200 ml) was added, and the mixture was extracted with dichloromethane. The dichloromethane layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane to give 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetohydrazide (2.93 g, 89.6%) as colorless crystals.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-5d920913e33e42dab57163cbcb8d7f5c
Source dataset
uspto-grants-2000_04
Patent number
US06048885

Reaction notes

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