Hydrochloric Acid → 4-(2-Cyano-5,7,7,10,10-pentamethyl-7,8,9,10-tetrahydro-5H-5,13-diaza-benzo[4,5]-cyclohepta[1,2-b]naphthalen-12-yl)benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-amino-4-[methyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amino]benzonitrile (32) (R4=CH3, 30.0 mmol), terephthalic acid monomethyl ester (30.0 mmol), POCl3 (69.0 mmol), and toluene (200 mL) is heated at 80° C. for 3 days. After cooling, the reaction mixture is treated with 1 N HCl (100 mL) and H2O (100 mL) and extracted with EtOAc. The organic layer is dried over MgSO4 and evaporated in vacuo. The residue is purified by flash column chromatography (hexane:EtOAc=5:1) to give (33) (R4=CH3, Z=H).

Provenance & Evidence