Diisopropylethylamine → N-[4-(3-Methylbutoxy)-2-nitrophenyl]-2-(3-methoxyphenoxy)acetamide

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Reaction Steps

A 1 L 3-neck flask fitted with a stir-bar, addition funnel, and an Ar inlet was charged with aniline 46b (12.0 g, 53.5 mmol) and CH2Cl2 (200 mL). The resultant solution was cooled in an ice bath and iPr2NEt (20.7 g, 28 mL, 161 mmol) was added followed by acid chloride 47b (12.9 g, 64.2 mmol) in CH2Cl2 (120 mL) over 10 min. The mixture was stirred at rt overnight. The red solution was diluted with CH2Cl2 (250 mL) and washed with saturated aqueous NH4Cl (200 mL), saturated NaHCO3 (200 mL), and brine (200 mL). The solution was filtered through phase separation paper and concentrated in vacuo to a red-brown solid. The solid was collected with EtOH (30 mL), pressed with rubber dam, and rinsed with EtOH (3×15 mL). The solid dried to give 15.0 g of 48b as a yellow solid (71%). 1H NMR (300 MHz, CDCl3): δ 9.78 (d, 1H), 7.73 (d, 1H), 7.29-7.22 (m, 2H), 6.68-6.60 (m, 3H), 4.65 (s, 2H), 4.05 (t, 2H), 3.86 (s, 3H), 1.86 (nonet, 1H), 1.72 (qt, 2H), 1.00 (d, 6H) ppm. HPLC analysis (0:10:90 H2O:A1:MeOH) showed a purity of 97% with a retention time of 6.2 min.

Provenance & Evidence