Ethanol → Isopentylindol

HRID 1957752Notes

Reaction equation

HRID 1957752 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=O)[CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13].[NH2-].[Na+].C1C2C(=CC=CC=2)CCC1.C(O)C>O>[CH3:13][CH:12]([CH3:14])[CH2:11][CH2:10][C:9]1[NH:8][C:3]2[C:2]([CH:1]=1)=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

6

Reactant 4

HCID 702EthanolHCID 8404TetralinHCID 24533Sodium amideHCID 22708317N-(2-methylphenyl)-4-methylvaleramide

Product 1

HCID 11041488IsopentylindolYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The following procedure is cited in Bull. Soc. Chim. Fr. (37):190 (1925). N-(2-methylphenyl)-4-methylvaleramide (20.5 g), sodium amide (90%) (11.0 g), and tetralin (100 ml) were mixed in a 500 ml round bottom flask equipped with a magnetic stirrer and reflux condenser and heated at reflux for 2 hours. After cooling to room temperature, ethanol (10 ml) was added, followed by H2O (150 ml). The layers were separated, the organic layer was filtered through a pad of anhydrous magnesium sulfate, and the solution was placed in a 200 ml round bottom flask equipped with a 10-inch vacuum jacketed Vigreux column. Tetralin was distilled at 35°-45° C./0.5 mm Hg. The residue was transferred to a 50 ml round bottom flask equipped with a 4-inch Vigreux column, and distillation at 118°-129°C./0.5 mm Hg provided 2-(3-methyl-n-butyl)-indole 13.1 g (70%) as a slightly yellow solid.

Workup

  1. customequipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureheated
  4. temperatureat reflux for 2 hours
  5. customThe layers were separated
  6. filtrationthe organic layer was filtered through a pad of anhydrous magnesium sulfate
  7. customthe solution was placed in a 200 ml round bottom flask
  8. customequipped with a 10-inch vacuum
  9. distillationTetralin was distilled at 35°-45° C./0.5 mm Hg
  10. customThe residue was transferred to a 50 ml round bottom flask
  11. customequipped with a 4-inch Vigreux column, and distillation at 118°-129°C./0.5 mm Hg

Sources & evidence

ORD record
ord-f190e0e6b448495288b83cc935e2ede5
Source dataset
uspto-grants-1998_07
Patent number
US05786488

Reaction notes

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