Reaction #488325

Reaction equation

2-(3,4-dimethoxyphenyl)acetic acid

N,O-dimethylhydroxylamine hydrochloride

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

hydroxybenzotriazole

triethylamine

→

2-(3,4-dimethoxyphenyl)-N-methoxy-N-methylacetamide

Yield 30.3%

Solvents

water

dichloromethane

Conditions

Workup

1. 1
   Extractionextracted with EtOAc (30 mL×3)
2. 2
   DryingThe combined organic layer was dried over Na2SO4
3. 3
   Concentrationconcentrated in vacuo
4. 4
   Otherpurified by column chromatography (PE: EtOAc=8:1)

Procedure

A mixture of 2-(3,4-dimethoxyphenyl)acetic acid (1 g, 5.1 mmol), N,O-dimethylhydroxylamine hydrochloride (480 mg, 5.1 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (978 mg, 5.1 mmol), hydroxybenzotriazole (690 mg, 5.1 mmol) and triethylamine (2.57 g, 25.5 mmol) in dichloromethane (30 mL) was stirred at room temperature overnight. The reaction mixture was diluted with water (30 mL), and extracted with EtOAc (30 mL×3). The combined organic layer was dried over Na2SO4, concentrated in vacuo, and purified by column chromatography (PE: EtOAc=8:1) to afford 2-(3,4-dimethoxyphenyl)-N-methoxy-N-methylacetamide (370 mg, yield 30.3%).

Source