Hydroxyamine hydrochloride → HCID 54400138, compound

Participants

Reaction Steps

A mixture of NaOMe (25 wt % in MeOH, 1.02 mL, 4.46 mmol), MeOH (4 mL), and hydroxylamine hydrochloride (310 mg, 4.46 mmol) was heated at reflux for 20 minutes. 5-Chloro-2-naphthalenylacetonitrile (600 mg, 2.98 mmol) and additional MeOH (4 mL) were added and heating was continued overnight. Additional hydroxylamine hydrochloride (150 mg, 2.16 mmol) and NaOMe (25 wt % in MeOH, 490 μL, 2.14 mmol) were added and heating was resumed for 4 hours. The mixture was cooled, concentrated, and suspended in H2O. The solid was collected by filtration and triturated with ether to give a pale yellow solid (478 mg, 69%), m.p. 121°-125° C.

Provenance & Evidence