Hydroxyamine hydrochloride → HCID 86685510, compound

HRID 1037065Notes

Reaction equation

HRID 1037065 reaction equation
[Cl:1][C:2]1[C:13]([CH:14]=O)=[CH:12][C:5]2[B:6]([OH:11])[O:7][C:8]([CH3:10])([CH3:9])[C:4]=2[CH:3]=1.[NH2:16][OH:17].Cl.CC([O-])=O.[Na+]>C1COCC1.O>[Cl:1][C:2]1[C:13]([CH:14]=[N:16][OH:17])=[CH:12][C:5]2[B:6]([OH:11])[O:7][C:8]([CH3:10])([CH3:9])[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86685509HCID 86685509, compound

Product 1

HCID 86685510HCID 86685510, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-chloro-1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbaldehyde (200 mg, 0.89 mmol) and NH2OH.HCl (74 mg, 1.07 mmol) in THF (12 mL) and H2O (3 mL) at rt was added NaOAc (110 mg, 1.34 mmol). The reaction mixture was stirred for 2 h and diluted with H2O. The mixture was extracted with EA and the organic layer was separated. The organic solution was washed with brine, dried over Na2SO4, filtered and concentrated to give crude compound 5-chloro-1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbaldehyde oxime as a light yellow solid. It was used in next step without further purification.

Workup

  1. extractionThe mixture was extracted with EA
  2. customthe organic layer was separated
  3. washThe organic solution was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-16f307e753bb4b938bbb9d82e9683f4f
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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