Hydroxylamine → Tert-butyl (2-{3-[amino(hydroxyimino)methyl]phenyl}ethoxy)acetate

Participants

Reaction Steps

tert-butyl [2-(3-cyanophenyl)ethoxy]acetate obtained in step 1 (1.42 g; 5.43 mmol) was dissolved in EtOH (28.40 mL) to which was added hydroxylamine (401.26 μL; 50%, 27.17 mmol). Reaction mixture was stirred at RT for 18 h after which solvents were removed under vacuum, solubilized in a water/ACN mixture (1:1) and lyophilized to give the desired compound as a sticky colorless oil (1.32 g; 82%). 1H NMR (DMSO-d6, 300 MHz) δ 9.56 (bs, 1H), 7.53-7.48 (m, 2H), 7.27-7.25 (m, 2H), 5.76 (bs, 2H), 3.96 (s, 2H), 3.67 (t, J=6.9 Hz, 2H), 2.83 (t, J=6.5 Hz, 2H). LC/MS (Method B): 295.2 (M+H)+.

Provenance & Evidence