453585-05-2

Basic information

• Product Name: C₁₆H₁₅NO₃
• CAS NO: 453585-05-2
• Molecular Weight: 269.3
• Mol File: 453585-05-2.mol

Chemical Properties

• CAS DataBase Reference: C₁₆H₁₅NO₃(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₆H₁₅NO₃(453585-05-2)
• EPA Substance Registry System: C₁₆H₁₅NO₃(453585-05-2)

Safety Data

• Hazardous Substances Data: 453585-05-2(Hazardous Substances Data)

Upstream product

• 4376-18-5 Monomethyl phthalate 
• 95-53-4 o-toluidine 
• 67-56-1 methanol 
• 19336-68-6 2-[(2'-methylphenylamido)]benzoic acid 
• 85-44-9 phthalic anhydride 

Downstream Products

• 2464-33-7 N-(2-methylphenyl)phthalimide 

Relevant articles and documents

An expeditious synthesis of imides from phthalic, maleic and succinic anhydrides and chemoselective C=C reduction of maleic amide esters

Phthalic, maleic and succinic anhydrides have been reacted with aromatic amines to obtain the corresponding monoacid monoamides. The latter have been each transformed into the corresponding cyclic imide derivatives by treating with SOCl2. Alternatively, anhydrides have been reacted with methanolic KOH to obtain monomethyl ester derivatives which on reaction with aromatic amines in the presence of EDC. HCl and HOBt give cyclic imide derivatives. Reaction of monoacid monoamides independently, with SOCl 2 at 0-5°C give the monoamide monoester derivatives. Treatment of monoamide monoester of malic anhydride with NaBH4 leads to the unusual reduction of C=C grouping as well as the carbonyl group of the ester group to from monoamide monoalcohol of succinic anhydride. Preparation of monoamide monoalcohol of succinic anhydride can also be achieved by chemoselective reduction of monoamide monoester of malic anhydride with Mg turnings yielding monoamide monoester of succinic anhydride followed by reduction of the latter with NaBH4.

A facile and green synthesis of N-substituted imides

Anhydrides 1, 6 and 10 have been reacted, independently, with aromatic primary amines 2 in solid phase by simple physical grinding of reactants with p-toluenesulphonicacid as a catalyst to yield corresponding open chain derivatives, monoacid monoamides3,7 and 11 respectively. The latter have each been transformed into the corresponding cyclic derivatives, i.e. imides 5, 9 and 13 respectively in solid phase by simple physical grinding of each with K 2CO3, alkylating agent and tetrabutylammoniumbromide as a catalyst with short reaction times. These cyclic imides can also be obtained by physical grinding of each of 3, 7 and 11 with dicyclohexylcarbodimide as a dehydrating agent in solid phase.