3-nitropthalic acid and its anhydrides was chosen as a starting material due to its ready availability and to the fact that it can be easily converted to diamine derivative 5 and 10, a compound that can be selectively functionalized at the amino positions. The electron donor groups chosen for this study were pyridyl, 1,3-dithiolanyl, benzyloximate, and thiophenyl ether, all known for their Lewis basicity and ligating potential. This investigation reflects our ongoing interest in synthesizing new organic ligands for supramolecular design. The initial step is the functionalization described herein was the conversion of 3-nitropthalic anhydride and 3-nitropthalic acid to 2,6-diamino benzoic acid methyl ester (5) and 2,3-diamino benzoic acid methyl ester (10) 3-nitrophthalic anhydride under methanol reflux conditions gives mixture of 1 and 6 in ratio of 9:1 (by NMR) in 98% yield. The mixture on treatment with thionyl chloride under heating condition gives corresponding mixture of acid chlorides 2 and 7 from which the acyl azide 3 and 8 were prepared by treating with sodium azide in acetone in 90%. The mixture of acyl azides 3 and 8 under Curtius rearrangement followed by column chromatography purification gives two isolated product 4 and 9 in 70% and 5% respectively. The compound 4 under palladium charcoal treatment gives product 5 in 90% yields. The compound 9 was independently prepared in four steps by regioselective esterfication of 3nitro phthalic acid, followed by its acid chloride 7 in 95% yield, which on acyl azide conversions 8 in 70% yield, followed by and Curties rearrangement. In these it is 100% regioselective conversion, no trace of its corresponding isomer was detected even in crude NMR. The compound 9 under reduction by using palladium charcoal condition gives the 2,3-diamino benzoic acid methyl ester 10 in 80% yield, and acetonide protected diamine 16 (in 5%), is obtained as byproduct. The mechanism is unclear.