Hydroxylamine → N-(1,2,3,4-Tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)-N'-hydroxyterephthalamide

Participants

Reaction Steps

To a solution of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-terephthalamic acid methyl ester 7 (0.20 g, 0.55 mmol) in MeOH (2 mL) was added an hydroxylamine solution (1.76 M, 2 mL) in MeOH and the reaction mixture was stirred 1 h at room temperature under magnetic stirring. The reaction mixture was adjusted to pH=5, concentrated and the residue was partitioned between EtOAc and H2O. The organic layer was dried with Na2SO4 and the product was crystallized by dissolving the mixture at 80° C. in CH3CN to give N-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)-N′-hydroxyterephthalamide EHT 7706 (0.05 g, 25% yield) as a white solid.

Provenance & Evidence