Aniline → 2-Methyl-3-pentyl indole

HRID 985711Notes

Reaction equation

HRID 985711 reaction equation
[CH:1]#[C:2][CH:3](O)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=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].C(OCC)C>[CH3:1][C:2]1[NH:10][C:11]2[C:16]([C:3]=1[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:15][CH:14]=[CH:13][CH:12]=2

Participants

6

Reactant 3

HCID 6115AnilineHCID 8870Benzenamine hydrochloride (1:1)HCID 131661-Octyn-3-ol

Product 1

HCID 122748892-Methyl-3-pentyl indoleYield 105%

Reagents, catalysts & solvents 2

HCID 6096991Triruthenium dodecacarbonylCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
140 °C

Procedure

1-Octyne-3-ol (1.136 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 9 hours. After cooling, diethyl ether (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 an 11:1 mixture of 3-methyl-2-pentyl indole and 2-methyl-3-pentyl indole (1.262 g; 6.3 mmol; yield, 95%; purity, about 95% or more) 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 an 11:1 mixture of 3-methyl-2-pentyl indole

Sources & evidence

ORD record
ord-dc33e580257747f38bd7d23fe29ec329
Source dataset
uspto-grants-2005_03
Patent number
US06872835B2

Reaction notes

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