Reaktion #465422

Reaktionsgleichung

EDCI

HOBt

triethylamine

N,O-dimethylhydroxylamine hydrochloride

(3,4-Dimethoxyphenyl)acetic acid

→

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

Ausbeute 66.1%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas evaporated at reduced pressure
2. 2
   SonstigeThe residue was partitioned between EtOAc and water
3. 3
   WaschenThe organic layer was washed with aq. HCl
4. 4
   Trocknendried (Na2SO4)
5. 5
   Einengenconcentrated in vacuo

Vorschrift

(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.

Quelle