Benzyloxyamine hydrochloride → 4-(Benzyloxyiminomethyl)-2,5-dimethylaniline

HRID 1627984Notes

Reaction equation

HRID 1627984 reaction equation
[NH2:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([CH:6]=O)=[C:4]([CH3:11])[CH:3]=1.Cl.[CH2:13]([O:20][NH2:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CO>[CH2:13]([O:20][N:21]=[CH:6][C:5]1[C:4]([CH3:11])=[CH:3][C:2]([NH2:1])=[C:9]([CH3:10])[CH:8]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 102312Benzyloxyamine hydrochlorideHCID 552846924-Amino-2,5-dimethylbenzaldehyde

Product 1

HCID 866385294-(Benzyloxyiminomethyl)-2,5-dimethylanilineYield 47.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.50 g (2.51 mmol) of 4-amino-2,5-dimethylbenzaldehyde is initially charged in 10 ml of methanol, 0.40 g (3.27 mmol) of O-benzyl hydroxylamine hydrochloride is added at room temperature and the reaction mixture is heated under reflux for 18 h. The mixture is then concentrated using a rotary evaporator and the residue is taken up in dichloromethane, extracted twice with water, dried over Na2SO4 and freed from the solvent under reduced pressure. This gives 0.3.8 g of product (purity 82.0%, yield 47.7%, log P (pH 2.3)=4.22).

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 18 h
  3. concentrationThe mixture is then concentrated
  4. customa rotary evaporator
  5. extractionextracted twice with water
  6. dry with materialdried over Na2SO4
  7. customThis gives 0.3.8 g of product (purity 82.0%, yield 47.7%, log P (pH 2.3)=4.22)

Sources & evidence

ORD record
ord-e02278f35d4e4b618b49d4589e838312
Source dataset
uspto-grants-2014_07
Patent number
US08785692B2

Reaction notes

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