Sodium Hydroxide → N-[(4-fluorophenyl)methylidene]hydroxylamine

HRID 606069Notes

Reaction equation

HRID 606069 reaction equation
[OH-:1].[Na+].[F:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.Cl.[NH2:13]O>C(O)C.O>[F:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[N:13][OH:1])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 680234-FluorobenzaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 68017N-[(4-fluorophenyl)methylidene]hydroxylamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Aqueous sodium hydroxide (70 mL of 50% w/w) was added to a solution of 4-fluorobenzaldehyde (140.5 g, 1.132 mol) and hydroxylamine hydrochloride (86.5 g, 1.25 mol) in ethanol (1 L) and water (2 L), and the reaction was stirred at room temperature for one hour and then adjusted to pH 14 with the addition of 50% w/w aqueous sodium hydroxide. The mixture was extracted with several portions of dichloromethane and then several portions of chloroform. The combined extracts were concentrated under reduced pressure approximately one liter, filtered through a layer of CELITE filter agent and sodium sulfate, and concentrated again under reduced pressure to yield 127 g of 4-fluorobenzaldehyde oxime as a white solid.

Workup

  1. extractionThe mixture was extracted with several portions of dichloromethane
  2. concentrationThe combined extracts were concentrated under reduced pressure approximately one liter
  3. filtrationfiltered through a layer of CELITE filter agent and sodium sulfate
  4. concentrationconcentrated again under reduced pressure

Sources & evidence

ORD record
ord-acbb4399280e4f5c8eafa7ee82934823
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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