Aniline → 2,3-Dimethylindole

HRID 985710Notes

Reaction equation

HRID 985710 reaction equation
[CH3:1][CH:2](O)[C:3]#[CH:4].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl.NC1C=CC=CC=1>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Ru].[Ru].[Ru].ClCCl>[CH3:1][C:2]1[NH:6][C:7]2[C:12]([C:3]=1[CH3:4])=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

6

Reactant 3

HCID 6115AnilineHCID 8870Benzenamine hydrochloride (1:1)HCID 162393-Butyn-2-ol

Product 1

HCID 70532,3-DimethylindoleYield 90%

Reagents, catalysts & solvents 2

HCID 6096991Triruthenium dodecacarbonylCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

3-Butine-2-ol (0.701 g, 10 mmol), aniline (0.931 g, 10 mmol), Ru3(CO)12 (32.0 mg, 0.05 mmol) and aniline hydrochloride (0.259 g, 2.0 mmol) were placed in a 10 ml round-bottomed flask, and the mixture was stirred at 120° C. for 12 hours. After cooling, dichloromethane (3 mL) was added, and the organic layer was washed twice with 1 M hydrochloric acid (2 mL) and once with water (2 mL). The organic layer was dried over sodium sulfate, and the solvent was distilled away, whereby 2,3-dimethyl indole (1.31 g; 9.0 mmol; yield, 90%; purity, about 99%) was obtained.

Workup

  1. temperatureAfter cooling
  2. washthe organic layer was washed twice with 1 M hydrochloric acid (2 mL) and once with water (2 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-1e10e1370be848d0a6e1920a0ac1f484
Source dataset
uspto-grants-2005_03
Patent number
US06872835B2

Reaction notes

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