2-(3-Ethoxyphenoxy)-N-(4-hydroxy-2-nitrophenyl)acetamide → N-(2-Amino-4-hydroxyphenyl)-2-(3-ethoxyphenoxy)acetamide

Participants

Reaction Steps

A 2 L hydrogenation vessel was charged with phenol 63b (12.1 g, 36.4 mmol) and THF (240 mL). To the resultant solution was added 10% Pd/C (1.2 g), and the mixture was hydrogenated at 49 psi for 2 hr. The catalyst was filtered off on glass fiber paper, and concentrated to a red oil. The crude oil crystallized with CH2Cl2 and was triturated with CH2Cl2:hexanes 1:1 (100 mL). The crystals were filtered, pressed with rubber dam, and rinsed with CH2Cl2:hexanes 1:1 (2×20 mL). The crystals were dried to give 10.1 g of 64 as yellow crystals (92%). HPLC analysis (10:10:80 H2O:A1:MeOH) showed a purity of greater than 99% with a retention time of 3.1 min.

Provenance & Evidence