Hydrazine → 4-Amino-2-(4-amino-2-hydroxybutoxy)benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-(4-(1,3-dioxoisoindolin-2-yl)-2-hydroxybutoxy)-4-nitrobenzonitrile (2.96 g, 7.76 mmol) in EtOH (28.1 mL) was added hydrazine (12.18 mL, 388 mmol). The reaction mixture was heated at 50° C. for 1.5 h. The reaction mixture was cooled to rt and filtered. The filtrate was concentrated and taken up in CH2Cl2. The solid was filtered off again, and the filtrate was concentrated and purified by Prep-HPLC to obtain 4-amino-2-(4-amino-2-hydroxybutoxy)benzonitrile (1.015 g, 59.1% yield). LC-MS (M+H)+=222.1. 1H NMR (500 MHz, methanol-d4) δ 7.24 (d, J=8.5 Hz, 1H), 6.35-6.26 (m, 2H), 4.17-4.09 (m, 1H), 4.05 (dd, J=9.5, 4.9 Hz, 1H), 3.97 (dd, J=9.5, 5.5 Hz, 1H), 3.20 (t, J=7.0 Hz, 2H), 2.08 (td, J=7.1, 3.5 Hz, 1H), 2.01-1.86 (m, 1H).

Provenance & Evidence