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

HRID 892203Notes

Reaction equation

HRID 892203 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-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 6-methoxy-1,3,3-trimethyl-1,3-dihydro-indol-2-one (601 mg, 2.93 mmol, example 79) 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 the title compound as an off white solid. MS (ESI) 192 (M+H)+.

Workup

  1. temperatureThe resulting solution is heated
  2. temperaturecooled to room temp
  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-cacefbc016e54dc696193dda239e8cb0
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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