Sodium Hydroxide → HCID 53726168, compound

HRID 1739661Notes

Reaction equation

HRID 1739661 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][O:16][C:17]1[C:22]([Cl:23])=[CH:21][C:20]([C:24]([O:26]C)=[O:25])=[CH:19][N:18]=1)[C:5]([NH:7][CH3:8])=[O:6].[OH-].[Na+]>CO>[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][O:16][C:17]1[C:22]([Cl:23])=[CH:21][C:20]([C:24]([OH:26])=[O:25])=[CH:19][N:18]=1)[C:5]([NH:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54417588HCID 54417588, compound

Product 1

HCID 53726168HCID 53726168, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

α-(Methoxyimino)-N-methyl-2-[[[3-chloro-5-(methoxycarbonyl)-2-pyridinyl]oxy]methyl]-benzeneacetamide (15.8 g, 40.4 mmol), prepared utilizing the general procedure described in Example 37, was dissolved in warm methanol (600 mL) to which was added 0.1 N NaOH (600 mL). The solution was stirred at room temperature overnight, then concentrated in vacuo to remove excess methanol. The remainder was extracted with Et2O (200 mL). The aqueous layer was acidified slightly (pH 5-6) resulting in a white precipitate. After 30 minutes of stirring at room temperature, the solid was collected, washed with water and dried in a vacuum oven to give α-(methoxyimino)-N-methyl-2-[[[3-chloro-5-(carboxy)-2-pyridinyl]oxy]methyl]-benzeneacetamide (14.9 g). M.P. 189-195° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove excess methanol
  3. extractionThe remainder was extracted with Et2O (200 mL)
  4. customresulting in a white precipitate
  5. stirringAfter 30 minutes of stirring at room temperature
  6. customthe solid was collected
  7. washwashed with water
  8. customdried in a vacuum oven

Sources & evidence

ORD record
ord-5ac40118baf242579fc79e0c66cac137
Source dataset
uspto-grants-1999_10
Patent number
US05968875

Reaction notes

Loading…