Methyl Anthranilate → trans-1-(2-Methoxycarbonylanilino)-2-ethoxycarbonylaminoindane

Participants

Reaction Steps

trans-1-Chloro-2-ethoxycarbonylaminoindane (20 g, 0.084 moles) was treated with methyl anthranilate (60 ml) and stirred under nitrogen at 60° for 5 hr. The resulting viscous mixture was diluted with ether (500 ml), washed exhaustively with 2.5N HCl (8×250 ml), and then with saturated sodium bicarbonate followed by brine. After drying (Na2SO4) and concentration in vacuo a brown solid (25.7 g) was obtained. Crystallisation from pentane/ether afforded the title compound (14 g; 58%) m.p. 108°-110°. Concentration of mother liquors gave a less pure second crop (2.6 g).

Provenance & Evidence