Benzenepropanoyl chloride → HCID 2852196, compound

Participants

Reaction Steps

A 500 mL 3-neck flask fitted with a stir-bar, addition funnel, and an Ar inlet was charged with aniline 46a (4.00 g, 22.0 mmol) and CH2Cl2 (80 mL). To the resultant solution was added iPr2NEt (7.10 g, 55.0 mmol) followed by acid chloride 74 (4.27 g, 25.3 mmol) in CH2Cl2 (40 mL) over 15 min. The mixture stirred at rt overnight. Another 0.75 g of acid chloride 74 was added, and the mixture stirred 2 hr to completion as monitored by HPLC. The solution was diluted with CH2Cl2 (100 mL) and washed with saturated aqueous NaHCO3 (125 mL) and brine (100 mL). The solution was filtered through phase separation paper and concentrated in vacuo to an oil/solid mix. The solid was collected with hexanes:EtOAc 4:1 (30 mL) and rinsed with hexanes:EtOAc 4:1 (2×10 mL). The material was dried to give 4.85 g of 75 as an orange solid (70%). 1H NMR (60 MHz, CDCl3): δ 9.8 (bs, 1H), 8.8 (d, 1H), 7.9 (d, 1H), 7.6 (s, 5H), 7.4 (d, 1H), 4.2 (qt, 2H), 3.1 (m, 4H), 1.5 (t, 3H) ppm. HPLC analysis (15:10:75 H2O:A1:MeOH) showed a purity of 98% with a retention time of 6.9 min.

Provenance & Evidence