Sodium Hydroxide → HCID 20134508, compound

Participants

Reaction Conditions

Reaction Steps

A mixture containing 6.55 g of 4-amino-N-tert-butyl-3,5-dichloro-β-methoxyphenethylamine hydrochloride in 66 ml of 50% hypophosphorous acid is cooled to 5° C. and 1.52 g of NaNO2 in 15 ml of H2O is added dropwise. Rapid foaming occurs from gas evolution and after 0.5 hours at 5° C., the mixture is stirred further at room temperature for two hours. It is then made alkaline with 50% aqueous NaOH solution, and the mixture is kept at below 25° C. with addition of ice. The mixture is extracted with 3×100 ml of CH2Cl2 and the combined organic phases are washed with 200 ml of brine, dried (MgSO4), and evaporated to dryness in vacuo to give 5.1 g of the title compound in the form of the free base. This product is dissolved in 50 ml of EtOH and acidified at 5° with 4 4N HCl to afford a light orange precipitate, which is collected. This gives 3.36 g, mp 278°-280° dec, of the title compound which is recrystallized from isopropanol to give 2.35 g, mp 280° C. dec.

Provenance & Evidence