Hydroxyamine hydrochloride → 4-Fluoro-naphthalene-1-carbaldehyde oxime

HRID 388375Notes

Reaction equation

HRID 388375 reaction equation
C([O-])(=O)C.[Na+].Cl.[NH2:7][OH:8].[F:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH:20]=O)=[CH:12][CH:11]=1>C1COCC1.O>[F:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH:20]=[N:7][OH:8])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 70225244-Fluoronaphthalene-1-carbaldehyde

Product 1

HCID 866581594-Fluoro-naphthalene-1-carbaldehyde oxime

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium acetate (4.8 g) is added to a solution of hydroxylamine hydrochloride (2.9 g) and 4-fluoro-naphthalene-1-carbaldehyde (8.1 g, example 1 step B) in THF (40 ml) and water (10 ml). After 3 hours at room temperature, the reaction is quenched with water and ethyl acetate. The organic, phase is separated and the water phase is extracted with ethyl acetate. The combined organic phases are washed with water and with a saturated aqueous solution of NaCl, dried over Mg2SO4 and concentrated in vacuo to yield 4-fluoro-naphthalene-1-carbaldehyde oxime. The crude product obtained is used without further purification.

Workup

  1. customthe reaction is quenched with water and ethyl acetate
  2. customThe organic, phase is separated
  3. extractionthe water phase is extracted with ethyl acetate
  4. washThe combined organic phases are washed with water and with a saturated aqueous solution of NaCl
  5. dry with materialdried over Mg2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3b266ea26e3643ad97a7c9fef3778853
Source dataset
uspto-grants-2013_02
Patent number
US08377942B2

Reaction notes

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