Methanol → HCID 88287593, compound

HRID 1720567Notes

Reaction equation

HRID 1720567 reaction equation
CO.[OH-:3].[K+].[Cl:5][C:6]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2/[C:20](=[N:23]\[O:24][CH3:25])/[C:21]#N)=[CH:10][CH:9]=[CH:8][N:7]=1.[OH2:26]>>[Cl:5][C:6]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2/[C:20](=[N:23]\[O:24][CH3:25])/[C:21]([OH:26])=[O:3])=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14797Potassium HydroxideHCID 88287604HCID 88287604, compound

Product 1

HCID 88287593HCID 88287593, compoundYield 42.8%

Procedure

Methanol (2 ml) and a 50% aqueous solution of potassium hydroxide (0.07 g, 0.66 mmol) were added to (E)-2-(2-chloro-3-pyridyloxymethyl)-a-methoxyiminophenylacetonitrile (0.11 g, 0.33 mmol). The mixture was stirred under reflux for 6 hours. After completion of the reaction, water (100 ml) was added, and the resulting 10 mixture was washed with methylene chloride (50 ml). Hydrochloric acid (1N, 1 ml) was added, and the mixture was extracted with methylene chloride (50 ml) twice. The methylene chloride layer was dried over anhydrous magnesium sulfate and evaporated under reduced pressure to dryness to give (E)-2-(2-chloro-3-pyridyloxymethyl)-α-methoxyiminophenylacetic acid (0.05 g, 42.8 %) as colorless crystals.

Workup

  1. temperatureunder reflux for 6 hours
  2. additionwas added
  3. washthe resulting 10 mixture was washed with methylene chloride (50 ml)
  4. additionHydrochloric acid (1N, 1 ml) was added
  5. extractionthe mixture was extracted with methylene chloride (50 ml) twice
  6. dry with materialThe methylene chloride layer was dried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure to dryness

Sources & evidence

ORD record
ord-c9be5a090f30488d90200e4ac1494581
Source dataset
uspto-grants-1996_04
Patent number
US05506358

Reaction notes

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