3-AMINO-1,2-PHTHALIC ACID, DIMETHYL ESTER

The synthesis of mIBX is readily accomplished from commercially available 3-nitrophtalic acid as follows: esterification of 3-nitrophtalic acid via the corresponding acid chloride to give nitrodiester (100percent), which upon catalytic hydrogenation provides the aminodiester (100percent). Diazotization is then performed, followed by iodination of the aminodiester to provide dimethyl 3-iodophthalate in about 91 percent yield. This is followed by saponification, then acidification of dimethyl 3-iodophthalate to give 3-iodophthalic acid in about 93 percent yield. 3-iodophthalic acid is then oxidized to form the water-soluble MIBX. (3) 5.40.2 3-Aminophthalic Acid Dimethyl Ester A mixture of 3:1 ethanol-conc. HCl (200 mL) was cooled to 0° C. and then 3-nitrophthalic acid dimethyl ester (15.0 g, 62.8 mmol) was added. Maintaining the cooling, tin chloride (70.8 g, 314 mmol) was added portionwise, over a period of 15 minutes. Following completion of the addition, the cooling bath was removed, and stirring proceeded at room temperature. After 2 hours, the mixture was neutralized by the addition of solid sodium bicarbonate, and the resulting mixture was extracted with ethyl acetate (3.x.150 mL) and the combined extracts were washed with water (5.x.250 mL), were dried (MgSOStep 2:[163] A mixture of 3:1 ethanol-conc. HCl (200 mL) was cooled to 0

Molecular Weight:209.20
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:209.06880783
Monoisotopic Mass:209.06880783
Topological Polar Surface Area:78.6
Heavy Atom Count:15
Complexity:254
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes