Aniline → 1H-Indole, 3-ethyl-2-methyl-

HRID 985712Notes

Reaction equation

HRID 985712 reaction equation
[CH:1]#[C:2][CH:3](O)[CH2:4][CH3:5].[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=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>[CH2:2]([C:3]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:4]=1[CH3:5])[CH3:1]

Participants

6

Reactant 3

HCID 6115AnilineHCID 8870Benzenamine hydrochloride (1:1)HCID 929811-Pentyn-3-ol

Product 1

HCID 1419851H-Indole, 3-ethyl-2-methyl-Yield 111.2%

Reagents, catalysts & solvents 2

HCID 6096991Triruthenium dodecacarbonylCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
140 °C

Procedure

1-Pentine-3-ol (0.757 g, 9 mmol), aniline (0.559 g, 6 mmol), Ru3(CO)12 (16.0 mg, 0.025 mmol) and aniline hydrochloride (0.130 g, 1.0 mmol) were placed in a 10 ml round-bottomed flask, and the mixture was stirred at 140° C. for 7.5 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 a 9.3:1 mixture of 2-ethyl-3-methyl indole and 3-ethyl-2-methyl indole (1.06 g; 6.67 mmol; yield, 95%) 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
  5. additionwhereby a 9.3:1 mixture of 2-ethyl-3-methyl indole

Sources & evidence

ORD record
ord-c7a41b2ffce64008bc5a2eb1b16429e7
Source dataset
uspto-grants-2005_03
Patent number
US06872835B2

Reaction notes

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