1-(2-Hydroxy-3-methylphenyl)ethan-1-one → 6-[1-(Hydroxyamino)ethylidene]-2-methylcyclohexa-2,4-dien-1-one

Participants

Reaction Conditions

Reaction Steps

1-(2-hydroxy-3-methylphenyl)ethanone (Step 46.1) (900 mg, 5.87 mmol) was dissolved in MeOH (15 mL) and NaOAc (771 mg, 9.40 mmol) and hydroxylamine hydrochloride (612 mg, 8.81 mmol) were successively added. The resulting mixture was heated up and stirred at 60° C. for 2 hr. The reaction mixture was poured into brine and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to afford the title product (964 mg, 5.25 mmol, 89% yield) as a colorless solid. tR: 0.94 min (LC-MS 2); ESI-MS: 166 [M+H]+, ESI-MS: 164 [M−H]− (LC-MS 2); Rf=0.66 (hexane/EtOAc 1:1).

Provenance & Evidence