M-Xylene → HCID 18788044, compound

HRID 1106393Notes

Reaction equation

HRID 1106393 reaction equation
[CH3:1][C:2](=[CH:4][N:5](CC(C)C)[C:6]1[CH:11]=CC=C[CH:7]=1)[CH3:3].[C:16]1([CH3:23])[CH:21]=[CH:20][CH:19]=[C:18](C)[CH:17]=1>ClCCl.[Cl-].[Zn+2].[Cl-]>[CH3:7][C:6]1([CH3:11])[CH2:23][C:16]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:5]1[CH2:4][CH:2]([CH3:3])[CH3:1]

Participants

5

Reactant 2

HCID 7929M-XyleneHCID 18788047HCID 18788047, compound

Product 1

HCID 18788044HCID 18788044, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(2-methylprop-2-en-3-yl)-N-isobutylaniline (6.1 g) and zinc chloride (3.9 g) in m-xylene (50 cm3) was heated under reflux for 24 hours before dissolving in dichloromethane and filtering. The dichloromethane solution was washed with water, separated and dried over anhydrous magnesium sulphate. The magnesium sulphate was removed by filtration and the dichloromethane was separated to leave a crude oil which was purified by elution from silica with a 9:1 mixture of hexane:dichloromethane. The solvent was evaporated to leave 2,2-dimethyl N-isobutylindoline (4.3 g, 71.4%) as a colourless oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. filtrationfiltering
  4. washThe dichloromethane solution was washed with water
  5. customseparated
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customThe magnesium sulphate was removed by filtration
  8. customthe dichloromethane was separated
  9. customto leave a crude oil which
  10. customwas purified by elution from silica with a 9:1 mixture of hexane
  11. customThe solvent was evaporated

Sources & evidence

ORD record
ord-974db245671842e68d51e9754f137b94
Source dataset
uspto-grants-2000_05
Patent number
US06057264

Reaction notes

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