Synthesis of 4-amino-N-isopropylbenzamide (178.1). To a solution of p-aminobenzoic acid (177.1, 0.6 g, 4.37 mmol, 1.0 eq.) in DMF (6 mL) was sequentially added isopropylamine (0.73 mL, 8.75 mmol, 2.0 eq.) and HATU (2.49 g, 6.55 mmol, 1.5 eq.). After cooling the reaction mixture to 0 °C, DIPEA (1.4 mL, 8.74 mmol, 2.0 eq.) was slowly added at 0 °C. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the mixture was poured into water and the product was extracted with EtOAc (3 x 20 mL). The organic layers were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography to afford 4-amino-N-isopropylbenzamide (178.1, 0.30 g, 38.5%) as a white solid.MS(ES): m/z 176.2 [M+H]+.
