Hydrochloric Acid → HCID 67396348, compound

Participants

Reaction Steps

To a degassed solution of methyl 4-[N-hydroxyethanimidoyl]-3-methylbenzoate (0.348 g, 1.68 mmol) and 12.0 M aqueous hydrochloric acid (0.35 mL, 4.20 mmol) in methanol (15 mL) was added 10% palladium on carbon (0.11 g, 0.101 mmol). The reaction mixture was stirred under a balloon atmosphere of H2 overnight. All insolubles were then removed via filtration through celite and the filtrate was evaporated to dryness. The residue was redissolved in methanol/toluene and concentrated under reduced pressure to afford a white solid (0.385 g, 100%). LC-MS: (FA) ES+ 195; 1H NMR (300 MHz, DMSO) δ 7.15 (m Hz, 2H), 6.73 (d, J=8.1 Hz, 1H), 6.45-6.26 (m, 1H), 3.96 (dd, J=13.7, 6.9 Hz, 1H), 3.10 (s, 3H), 1.67 (s, 3H), 0.80 (d, J=6.8 Hz, 3H).

Provenance & Evidence