Methyl iodide → 5-Methyl-5,6-dihydroindeno[2,1-b]indole

HRID 1280330Notes

Reaction equation

HRID 1280330 reaction equation
[OH-].[Na+].[CH:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]1[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][C:6]=1[NH:7]2.[CH3:19]I>[Br-].C[N+](C)(C)CCCCCCCCCCCCCCCC.C1C=CC=CC=1>[CH3:19][N:7]1[C:8]2[C:4](=[CH:3][CH:11]=[CH:10][CH:9]=2)[C:5]2[C:18]3[C:13]([CH2:12][C:6]1=2)=[CH:14][CH:15]=[CH:16][CH:17]=3

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 131294105,6-Dihydroindeno[2,1-b]indole

Product 1

HCID 131294115-Methyl-5,6-dihydroindeno[2,1-b]indoleYield 78.2%

Reagents, catalysts & solvents 2

HCID 5974Hexadecyltrimethylammonium BromideCatalystHCID 241BenzeneSolvent

Procedure

In a 0.5 l bulb were placed 100 ml 50% aqueous NaOH, 100 ml benzene, 6.1 g (28 mmol)of 5,6-dihydroindeno[2,1-b]indole, prepared in Example 4, 1.8 ml (28 mmol) of MeI and 0.5 g of trimethylcetylammonium bromide. After having stirred the obtained mixture for 2 hours, the formation of an organic phase was observed; said phase was separated, washed twice with water (100 ml) and dried over Na2SO4. After removal of the solvent, the residue was recrystallized from ethanol, obtaining 4.8 g of N-methyl-5,6-dihydroindeno[2,1-b]indole (yield=78%).

Workup

  1. customwas separated
  2. washwashed twice with water (100 ml)
  3. dry with materialdried over Na2SO4
  4. customAfter removal of the solvent
  5. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-e5eded4ba45a4b619e3d24c9e918ebc9
Source dataset
uspto-grants-2002_09
Patent number
US06451724B1

Reaction notes

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