Reaction #465422

Reaction equation

EDCI

HOBt

triethylamine

N,O-dimethylhydroxylamine hydrochloride

(3,4-Dimethoxyphenyl)acetic acid

→

N-methyl-N-methoxy-(3,4-dimethoxyphenyl)acetamide

Yield 66.1%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   Otherwas evaporated at reduced pressure
2. 2
   OtherThe residue was partitioned between EtOAc and water
3. 3
   WashThe organic layer was washed with aq. HCl
4. 4
   Dryingdried (Na2SO4)
5. 5
   Concentrationconcentrated in vacuo

Procedure

(3,4-Dimethoxyphenyl)acetic acid (13.0 g, 66.4 mmol) was suspended in anhydrous CH2Cl2 followed by addition of EDCI (15.3 g, 79.7 mmol), HOBt (20.6 g, 152 mmol), triethylamine (8.06 g, 79.7 mmol), and N,O-dimethylhydroxylamine hydrochloride (6.48 g, 66.4 mmol). The reaction was stirred 3 days at ambient temperature after which the solvent was evaporated at reduced pressure. The residue was partitioned between EtOAc and water. The organic layer was washed with aq. HCl, sat NaHCO3, brine, dried (Na2SO4), and concentrated in vacuo to give 10.5 g (66%) of N-methyl-N-methoxy-(3,4-dimethoxyphenyl)acetamide as a pale brown oil.

Source