Ethanol → HCID 73461926, compound

HRID 434027Notes

Reaction equation

HRID 434027 reaction equation
Cl[C:2]1[CH:9]=C[CH:7]=[C:6]([F:10])[C:3]=1C=O.[ClH:11].[NH2:12][OH:13].[OH-].[Na+].[CH2:16](O)[CH3:17]>O>[Cl:11][C:17]1[CH:16]=[CH:7][C:6]([F:10])=[CH:3][C:2]=1[CH:9]=[N:12][OH:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 678472-Chloro-6-fluorobenzaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 73461926HCID 73461926, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
27.5 °C

Procedure

To a mixture of 2-chloro-6-fluorobenzaldehyde (20 g, 0.126 mmoL) in water (30 mL), ethanol (35 mL) and ice (55 g) were added to hydroxylamine hydrochloride (9.64 g, 0.139 mmoL), then NaOH (12.6 g) in water (30 mL) was added with stirring. Enough ice was added to maintain temperature at 25-30° C. After 1 h, the mixture was washed with ether (150 mL) and acidified with concentrated HCl to a pH of 6 (ice was added to keep the temperature at 25-30° C.). The product was extracted with dichloromethane (2×200 mL), dried over MgSO4 and the solvent removed in vacuo to furnish the oxime as a white solid (17.2 g, 79.0%). mp 132.8-134.0° C.

Workup

  1. additionEnough ice was added
  2. washthe mixture was washed with ether (150 mL)
  3. additionwas added
  4. customat 25-30° C.
  5. extractionThe product was extracted with dichloromethane (2×200 mL)
  6. dry with materialdried over MgSO4
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a66d3af00ca14a46bc36e69a84d20f4d
Source dataset
uspto-grants-2003_12
Patent number
US06670373B1

Reaction notes

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