Triethylamine → 6-Methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

A solution of triethylamine (2.7 ml, 0.019 mol) and ethyl chloroformate (2 ml, 0.021 mol) in acetone (40 ml) is added to a solution of the acid obtained in step (i) (3 g, 0.014 mol) in acetone (50 ml) cooled to -10° C. After 1,5 hours at -10° C., concentrated NH4OH (4.5 ml, 0.036 mol) is added dropwise and the reaction mixture is allowed to stand at -10° C. for 1 hour and at room temperature overnight. The solution is concentrated under vacuum, ethyl acetate (150 ml) is added to the obtained residue and the solution is washed sequentially with water, a saturated sodium bicarbonate solution, 6N hydrochloric acid, and water, then it is dried and concentrated to dryness. The residue is triturated with isopropyl ether and filtered thus affording 1.7 g of the above indicated amide; m.p. 136°-138° C.; [α]=+40.2° (c= 1.4%, CHCl3).

Provenance & Evidence