Reaction #710526

Reaction equation

Compound I

2-(1,3-benzodioxol-5-yl)-2-methyl propanal

NH2OH

pyridine

→

Compound J

Yield 96.0%

2-(1,3-benzodioxol-5-yl)-2-methyl propanal oxime

Yield 96.0%

Solvents

ethanol

HCl

Conditions

Workup

1. 1
   OtherThe reaction mixture was evaporated to dryness
2. 2
   workup.ADDITIONadded 10 mL of ethyl acetate
3. 3
   WashThe organic layer was washed with distilled water
4. 4
   Dryingdried over anhydrous sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated
7. 7
   OtherThe crude reaction mixture
8. 8
   Otherwas purified over silica gel column

Procedure

To a solution of Compound I (511 mg, 2.66 mmol) in ethanol (1 mL), HCl.NH2OH (277 mg, 4.00 mmol) and pyridine (2.2 mL, 26.58 mmol) were added and it was stirred at room temperature for 1.5 hours. The reaction mixture was evaporated to dryness and added 10 mL of ethyl acetate. The organic layer was washed with distilled water, dried over anhydrous sodium sulfate, filtered and evaporated. The crude reaction mixture was purified over silica gel column using 5:1 petroleum ether-ethyl acetate as solvent to afford Compound J (528 mg, 96%) as a white foam.

Source