6-methoxy-2,3-dimethyl-1H-indole → 2,3-Dimethyl-1H-indol-6-ol

HRID 1826217Notes

Reaction equation

HRID 1826217 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH3:11])=[CH:8][CH:7]=[C:6]([O:12]C)[CH:5]=2.Cl.N1C=CC=CC=1>O>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH3:11])=[CH:8][CH:7]=[C:6]([OH:12])[CH:5]=2

Participants

4

Reactant 2

HCID 2665946-methoxy-2,3-dimethyl-1H-indoleHCID 10176127Pyridinium chloride

Product 1

HCID 221414062,3-Dimethyl-1H-indol-6-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

2,3-Dimethyl-6-methoxy-1H-indole (2.0 g; synthesized by the process reported by Ockenden et al., J. Chem. Soc., pp. 3175-3180 (1957)) was mixed with pyridine hydrochloride (7.91 g; mfd. by KANTO KAGAKU). The resulting mixture was stirred at 200° C. for 15 minutes and then cooled. After adding water (100 mL), the mixture was then extracted with ethyl acetate (100 mL). The organic layer was dried over anhydrous sodium sulfate (10 g). The solvent was distilled off under reduced pressure to yield crude 2,3-dimethyl-6-hydroxy-1H-indole (1.86 g) as a gray crystal.

Workup

  1. customsynthesized by the process
  2. temperaturecooled
  3. extractionthe mixture was then extracted with ethyl acetate (100 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate (10 g)
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-25317aea68bc4ed5b472ceaaaecbce39
Source dataset
uspto-grants-2006_05
Patent number
US07049445B2

Reaction notes

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