M-Xylene → HCID 18788046, compound

HRID 1106395Notes

Reaction equation

HRID 1106395 reaction equation
CC(=C[N:5]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:6]1[CH:11]=CC=C[CH:7]=1)C.[C:19]1([CH3:26])[CH:24]=[CH:23][CH:22]=[C:21](C)[CH:20]=1>ClCCl.[Cl-].[Zn+2].[Cl-]>[CH3:7][C:6]1([CH3:11])[CH2:26][C:19]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:5]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 7929M-XyleneHCID 53963027HCID 53963027, compound

Product 1

HCID 18788046HCID 18788046, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

N-(2-methylprop-2-en-3-yl)N-n-heptyl aniline (0.38 mole), zinc chloride (0.4 mole) and m-xylene (200 cm3) were refluxed for 17 hours before cooling and dissolving in dichloromethane. The dichloromethane was filtered and washed with water, separated, dried over magnesium sulphate, filtered and evaporated to leave an oil. The oil was eluted from silica using 50:50 dichloromethane/hexane as eluent evaporated of the solvent gave 2,2-dimethyl-N-n-heptylindoline (122 g, 95.8%).

Workup

  1. temperaturebefore cooling
  2. filtrationThe dichloromethane was filtered
  3. washwashed with water
  4. customseparated
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customto leave an oil
  9. washThe oil was eluted from silica using 50:50 dichloromethane/hexane as eluent
  10. customevaporated of the solvent

Sources & evidence

ORD record
ord-6bab9289b21a4160b75179ad43556adc
Source dataset
uspto-grants-2000_05
Patent number
US06057264

Reaction notes

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