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

HRID 982834Notes

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

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

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

Sources & evidence

ORD record: ord-adf8a250c7134758ae175e70bd31cc16
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06861444B2

Reaction notes

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