Reaction #62144

Reaction equation

4-(2-Quinolin-2-yl-ethyl)-benzoic acid

acetonitrile

O,N-Dimethyl-hydroxylamine hydrogen chloride

sodium hydroxide

→

title compound

Yield 88.0%

N-Methoxy-N-methyl-4-(2-quinolin-2-yl-ethyl)-benzamide

Yield 88.0%

Solvents

dioxane

triethylamine

Conditions

Workup

1. 1
   Extractionextracted with chloroform, dried magnesium sulfate
2. 2
   Filtrationfiltered
3. 3
   Concentrationconcentrated
4. 4
   WashBiotage MPLC chromatography eluting with 20-50% ethyl acetate

Procedure

To a solution of 4-(2-Quinolin-2-yl-ethyl)-benzoic acid (530 mg) in dioxane 5 ml/acetonitrile 5 ml was added triethylamine (0.60 ml) and O,N-Dimethyl-hydroxylamine hydrogen chloride (240 mg). After 72 h, the reaction mixture was poured into 1N sodium hydroxide solution and extracted with chloroform, dried magnesium sulfate, filtered and concentrated. Biotage MPLC chromatography eluting with 20-50% ethyl acetate provided the title compound (516 mg, 88%). MS: (M+H m/z=321.1).

Source