Hydroxyamine hydrochloride → 4-[1,2,4]Triazol-1-yl-naphthalene-1-carbaldehyde oxime

HRID 388365Notes

Reaction equation

HRID 388365 reaction equation
C([O-])(=O)C.[Na+].Cl.[NH2:7][OH:8].[N:9]1([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH:24]=O)=[CH:16][CH:15]=2)[CH:13]=[N:12][CH:11]=[N:10]1>C1COCC1.O.CS(C)=O>[N:9]1([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH:24]=[N:7][OH:8])=[CH:16][CH:15]=2)[CH:13]=[N:12][CH:11]=[N:10]1

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 866581554-[1,2,4]Triazol-1-yl-naphthalene-1-carbaldehyde

Product 1

HCID 866581564-[1,2,4]Triazol-1-yl-naphthalene-1-carbaldehyde oxime

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium acetate (262 mg) is added to a solution of hydroxylamine hydrochloride (193 mg) and 4-[1,2,4]triazol-1-yl-naphthalene-1-carbaldehyde (455 mg) in THF (16 ml), water (2 ml) and DMSO (2 ml). After 5 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 extracted with water and with a saturated aqueous solution of NaCl, dried over Na2SO4 and concentrated in vacuo to yield 4-[1,2,4]triazol-1-yl-naphthalene-1-carbaldehyde oxime. The crude product obtained (390 mg, beige crystals) is used without further purification. MS (HPLC/MS): 239 (MH+). Retention time 2.76 min.

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. extractionThe combined organic phases are extracted with water and with a saturated aqueous solution of NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-42201bdb632445db95456e9864989b36
Source dataset
uspto-grants-2013_02
Patent number
US08377942B2

Reaction notes

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