5-Nitrosalicylaldehyde → Phthalic Anhydride

Participants

Reaction Steps

The intermediates for reacting with 5-nitrosalicylaldehyde to prepare compounds wherein --Y-- contains an ethylbenzyl or ethoxybenzyl group were prepared by the reduction of the appropriate methyl cyanomethylbenzoate or cyanomethoxybenzoate with diborane in tetrahydrofuran solution, followed by the reaction of the amino compound thus obtained with phthalic anhydride at 100° C. and then with phosphorus tribromide also at 100° C. The various intermediates which were characterised have melting points as follows: 4-(2-aminoethyl)benzyl alcohol hydrochloride m.p. 160°-162° C. 3-(2-aminoethyl)benzyl alcohol hydrochloride m.p. 115°-118° C. 2-(2-aminoethyl)benzyl alcohol hydrochloride m.p. 103°-104° C. 4-(2-aminoethoxy)benzyl alcohol m.p. 92°-94° C. 3-(2-aminoethoxy)benzyl alcohol hydrochloride m.p. 143°-145° C. 4-(2-phthalimidoethyl)benzyl bromide 158°-161° C. 3-(2-phthalimidoethyl)benzyl bromide 93°-94° C. 2-(2-phthalimidoethyl)benzyl bromide 140°-141° C. 3-(2-phthalimidoethoxy)benzyl bromide 116°-117° C. 4-(2-phthalimidoethoxy)benzyl chloride 109°-112° C. (prepared by reacting with mesyl chloride and triethylamine in place of phosphorus tribromide).

Provenance & Evidence