Hydrogen Bromide → HCID 21966459, compound

Participants

Reaction Conditions

Reaction Steps

6-Methoxy-1-(4-methoxy-benzyl-3,3,5-trimethyl-1,3-dihydro-indol-2-one (640 mg, 1.97 mmol) was mixed with acetic acid (0.7 mL)and 48% hydrobromic acid (7 mL) and heated to reflux 12 hours. The solution was cooled to 0° C. and aqueous Na2CO3 was added to adjust to pH=7 then extracted with EtOAc, washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: EtOAc/4:1 to 1:1) to give 280 mg of 6-Hydroxy-3,3,5-trimethyl-1,3-dihydro-indol-2-one (74%). 1H NMR (300 MHz, DMSO-d6, ppm): δ: 1.15 (s, 6 H), 2.026.34 (s,1 H), 6.89 (s, 1 H), 9.21 (s,1 H), 10.01(s, 1 H).

Provenance & Evidence