Water → HCID 53825779, compound

HRID 1739660Notes

Reaction equation

HRID 1739660 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=[N:16][O:17][CH3:18])[C:12]([NH:14][CH3:15])=[O:13].[CH:19]([O:22][C:23](=[O:32])[C:24]1[CH:29]=[C:28]([Cl:30])[C:27](Cl)=[N:26][CH:25]=1)([CH3:21])[CH3:20].O>C1COCC1>[CH3:18][O:17][N:16]=[C:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH2:4][O:3][C:27]1[C:28]([Cl:30])=[CH:29][C:24]([C:23]([O:22][CH:19]([CH3:21])[CH3:20])=[O:32])=[CH:25][N:26]=1)[C:12]([NH:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 21836299HCID 21836299, compoundHCID 544725602-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide

Product 1

HCID 53825779HCID 53825779, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

NaH (60% dispersion in mineral oil, 0.23 g, 12.0 mmol) was washed (2×) with hexanes then suspended in THF (10 mL) to which 2-hydroxymethyl-α-methyoxyimino-N-methyl-benzeneacetamide (0.89 g, 4.0 mmol) in THF solution was added. The solution was stirred at room temperature for 10 minutes at which time isopropyl-5,6-dichloronicotinate (1.00 g, 4.3 mmol) in THF solution was added. After 15 minutes of stirring at room temperature, the solution was poured into 4-5 volumes of water and extracted with Et2O (2×100 mL) . The organics were dried over MgSO4 and concentrated to 1.5 g tan, viscous oil. Crude product was chromatographed using silica gel (230-400 mesh) with descending solvent gradient from 100% petroleum ether to 80/20 petroleum ether/ethyl acetate as the mobile phase. Elution and concentration gave α-(methoxyimino)-N-methyl-2-[[[3-chloro-5-(isopropoxycarbonyl)-2-pyridinyl]oxy]methyl]-benzeneacetamide (0.72 g) as a white solid.

Workup

  1. additionwas added
  2. additionwas added
  3. extractionextracted with Et2O (2×100 mL)
  4. dry with materialThe organics were dried over MgSO4
  5. concentrationconcentrated to 1.5 g tan
  6. customCrude product was chromatographed
  7. washElution and concentration

Sources & evidence

ORD record
ord-9f3bfb1616ef4bed9c2a4dff183a26a0
Source dataset
uspto-grants-1999_10
Patent number
US05968875

Reaction notes

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