Formaldehyde → HCID 13676511, compound

Participants

Reaction Conditions

Reaction Steps

Dimethylammonium chloride (2.34 g), formalin solution (1.58 g;37%) and concentrated hydrochloric acid (1 drop) was stirred at room temperature for 5 minutes then added to acetic anhydride (11.4 ml ). After about 20 minutes vigorous boiling occurred. 6-Acetamido-1-tetralone (3.6 g) was then added and the mixture was stirred at 100° C. for one hour. Evaporation of the reaction mixture under reduced pressure yielded an orange solid which was treated with acetone (15 ml ) for 3 minutes. The residue obtained on removal of acetone was dissolved in water (20 ml ) and treated with 2N sodium hydroxide to give pH 10. The precipitated oil was extracted with dichloromethane, dried (MgSO4) and evaporated to give crude 6-acetamido-2-dimethylaminomethyl-1-tetralone (5.0 g;M+ =260) which was taken up in acetone (30 ml ) and treated with iodomethane (12 ml ). The precipitate obtained was filtered off and washed with ether to give 6-acetamido-1-oxo-1,2,3,4-tetrahydro-2-naphthyl-trimethyl ammonium iodide (4.25 g; m.p. 168°-70°).

Provenance & Evidence