Hydrazine → HCID 175538, compound

Participants

Reaction Steps

Compound 8 (5 g, 15.8 mmol) was added to a solution of pure hydrazine (608 mg, 18.97 mmol, 1.2 equivalent) in 50 ml of ethyl alcohol and 4 ml of water. The mixture was refluxed for 2 h and then held at room temperature. The white solid (phthalhydrazide) was filtered. The filtrate was concentrated and the residue was redistributed in ethyl acetate and water. The water phase was extracted two times with ethyl acetate and the combined ethyl acetate phase was dried to give a yellowish solid as the HCl salt (9, 2.45 g, 70% yield). 1H NMR (D2O, δppm)(HCl salt): 2.91 (dd, 1H, NH2—CHa, J=13.2 Hz, 9.9 Hz), 3.21 (dd, 1H, NH2—CHb, J=13.2 Hz, 2.7 Hz), 4.19 (tt, 1H, HO—CH—, J=9.0 Hz, 3.0 Hz), 4.28 (dd, 1H, imidazole-CHa—, J=13.8 Hz, 8.7 Hz), 4.57 (dd, 1H, imidazole-CHb—, J=13.8 Hz, 2.7 Hz), 7.09 (d, 1H, J=0.9 Hz, —CH═), 7.35 (d, 1H, J=0.9 Hz, —CH═). 13C NMR (D2O, δppm): 42.06, 53.00, 66.86, 128.06, 128.92, 144.73.

Provenance & Evidence