4-Methylbenzoyl Chloride → Dimethyl 5-[(4-methylbenzoyl)amino]isophthalate

Participants

Reaction Steps

To 1.20 g (5.74 mmol) of methyl 5-amino-3-(methoxycarbonyl)benzoate, compound 87, suspended in 50 mL of chloroform and 1.05 mL (6.00 mmol) of diisopropylethylamine was added 836 μL (6.32 mmol) of p-toluoyl chloride in 10 mL of chloroform over 30 min. The reaction was allowed to stir at ambient temperature for 2 hr. Then, another 100 μL (0.60 mmol) of diisopropylethylamine and 100 μL (0.76 mmol) of p-toluoyl chloride in 2 mL of chloroform was added. After an addition 30 min, the volatiles were removed by rotary evaporation and the resulting residue was dissolved in ethyl acetate and extracted with 0.1 N aqueous NaOH followed by extraction with water. The organic layer was dried (MgSO4), filtered, and volatiles removed in vacuo. This provided 1.86 g (5.68 mmol) of the desired compound. The product was identified by 1H NMR and mass spectroscopy and purity was assessed by RP-HPLC.

Provenance & Evidence