Hydrogen Bromide → HCID 21966459, compound

HRID 2212607Notes

Reaction equation

HRID 2212607 reaction equation
COC1C=CC(C[N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=3)[C:10]([CH3:19])([CH3:18])[C:9]2=[O:20])=CC=1.Br.C([O-])([O-])=[O:25].[Na+].[Na+]>C(O)(=O)C>[OH:25][C:14]1[CH:15]=[C:16]2[C:11]([C:10]([CH3:19])([CH3:18])[C:9](=[O:20])[NH:8]2)=[CH:12][C:13]=1[CH3:17]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 10340Sodium CarbonateHCID 86590248HCID 86590248, compound

Product 1

HCID 21966459HCID 21966459, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

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).

Workup

  1. temperatureheated
  2. temperatureto reflux 12 hours
  3. extractionthen extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (hexane: EtOAc/4:1 to 1:1)

Sources & evidence

ORD record
ord-aba4ff9e6dfd47ae937e51930cc2ff89
Source dataset
uspto-grants-2006_09
Patent number
US07102000B2

Reaction notes

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