Ethylene Glycol → 1H-Benz(g)indole, 2,3-dimethyl-

HRID 985714Notes

Reaction equation

HRID 985714 reaction equation
[CH3:1][CH:2](O)[C:3]#[CH:4].[C:6]1([NH2:16])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.C(O)CO>[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].F[P-](F)(F)(F)(F)F.[NH4+].C(OCC)C>[CH3:1][C:2]1[NH:16][C:6]2[C:7]([C:3]=1[CH3:4])=[CH:8][CH:9]=[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=21

Participants

7

Reactant 3

HCID 174Ethylene GlycolHCID 86401-NaphthylamineHCID 162393-Butyn-2-ol

Product 1

HCID 1480211H-Benz(g)indole, 2,3-dimethyl-Yield 95%

Reagents, catalysts & solvents 3

HCID 6096991Triruthenium dodecacarbonylCatalystHCID 9793912Ammonium hexafluorophosphateCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
140 °C

Procedure

3-Butine-2-ol (0.631 g, 9 mmol), 1-napthylamine (0.859 g, 6 mmol), Ru3(CO)12 (16.0 mg, 0.025 mmol), ammonium hexafluorophosphate (0.041 g, 0.25 mmol) and 1 ml ethylene glycol were placed in a 10 ml round-bottomed flask, and the mixture was stirred at 140° C. for 20 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 2,3-dimethylbenzo[g]indole (1.113 g; 5.7 mmol; yield, 95%; purity, 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

Sources & evidence

ORD record
ord-e30b9eabd0284d05a2614cdc2d7ba6ab
Source dataset
uspto-grants-2005_03
Patent number
US06872835B2

Reaction notes

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