Hydrogen Bromide → 6-hydroxy-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-one

HRID 988257Notes

Reaction equation

HRID 988257 reaction equation
C[O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:15])([CH3:14])[C:8](=[O:13])[N:9]2[CH3:12])=[CH:5][CH:4]=1.Br>C(O)(=O)C>[OH:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:15])([CH3:14])[C:8](=[O:13])[N:9]2[CH3:12])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 219318586-Methoxy-1,3,3-trimethylindolin-2-one

Product 1

HCID 219317776-hydroxy-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-oneYield 88.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 6-methoxy-1,3,3-trimethyl-1,3-dihydro-indol-2-one (601 mg, 2.93 mmol) in acetic acid (880 μL) is added hydrobromic acid (48% in H2O) (8.8 mL). The resulting solution is heated to reflux (105°-110° C.), stirred 2 hrs, then cooled to room temp and concentrated under reduced pressure. The residue is dissolved in EtOAc and the organic layer washed with water, brine, dried over MgSO4 and concentrated. The residue is purified by triturating with a small volume of ether to give 495 mg of title compound as an off white solid. MS (ESI) 192 (M+H)+.

Workup

  1. temperatureThe resulting solution is heated
  2. temperatureto reflux (105°-110° C.)
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue is dissolved in EtOAc
  5. washthe organic layer washed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue is purified
  9. customby triturating with a small volume of ether

Sources & evidence

ORD record
ord-6a35bd728ef049bf88003f43df7d2006
Source dataset
uspto-grants-2003_10
Patent number
US06635655B1

Reaction notes

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