Hydroxyamine hydrochloride → (NE)-N-[(1-hydroxy-3,3-dimethyl-2,1-benzoxaborol-6-yl)methylidene]hydroxylamine

HRID 1037076Notes

Reaction equation

HRID 1037076 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([CH:11]=O)[CH:9]=[CH:10][C:5]=2[C:4]([CH3:14])([CH3:13])[O:3]1.[NH2:15][OH:16].Cl.CC([O-])=O.[Na+]>C1COCC1.O>[OH:1][B:2]1[C:6]2[CH:7]=[C:8](/[CH:11]=[N:15]/[OH:16])[CH:9]=[CH:10][C:5]=2[C:4]([CH3:14])([CH3:13])[O:3]1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 866854601-Hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbaldehyde

Product 1

HCID 89573772(NE)-N-[(1-hydroxy-3,3-dimethyl-2,1-benzoxaborol-6-yl)methylidene]hydroxylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbaldehyde (9.0 g, 47.4 mmol) and NH2OH.HCl (3.92 g, 56.9 mmol) in THF (100 mL) and H2O (25 mL) at rt was added NaOAc (5.83 g, 71.1 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 under reduced pressure to give crude compound (E)-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 under reduced pressure

Sources & evidence

ORD record
ord-f7f5ebccf42946cab53e28a76340ef7d
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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