Hydroxyamine hydrochloride → 4-Methyl-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-amine

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Reaction Steps

A 100-mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 150g (550 mg, 1.0 eq., 2.38 mmol), hydroxylamine hydrochloride (827 mg, 5.0 eq., 11.9 mmol), and ethanol (30 mL). The mixture was refluxed for 2 days. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by reverse-phase prep-HPLC to afford 150h (30 mg, 8%) as a yellow oil. MS-ESI: [M+H]+ 154.1. 1H NMR (500 MHz, CDCl3) δ 5.37 (s, 1H), 4.73 (q, J=7.0 Hz, 1H), 4.26-4.23 (m, 1H), 4.08-4.03 (m, 1H), 3.91-3.90 (m, 1H), 3.90-3.87 (m, 1H), 1.65 (d, J=7.0 Hz, 3H).

Provenance & Evidence