Methyl iodide → 5,8-Dimethyl-5,10-dihydroindeno[1,2-b]indole

HRID 1264126Notes

Reaction equation

HRID 1264126 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:12]=[CH:11][C:10]2[NH:9][C:8]3[C:13]4[C:18]([CH2:19][C:7]=3[C:6]=2[CH:5]=1)=[CH:17][CH:16]=[CH:15][CH:14]=4.[CH3:20]I>[Br-].C[N+](C)(C)CCCCCCCCCCCCCCCC.C1(C)C=CC=CC=1>[CH3:20][N:9]1[C:10]2[CH:11]=[CH:12][C:4]([CH3:3])=[CH:5][C:6]=2[C:7]2[CH2:19][C:18]3[C:13]([C:8]1=2)=[CH:14][CH:15]=[CH:16][CH:17]=3

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 222470798-Methyl-5,10-dihydroindeno[1,2-b]indole

Product 1

HCID 179536985,8-Dimethyl-5,10-dihydroindeno[1,2-b]indole

Reagents, catalysts & solvents 2

HCID 5974Hexadecyltrimethylammonium BromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

To a 100 mL of 50% aqueous NaOH solution is added 0.5 gram of trimethylcetylammonium bromide, 6.1 grams of 8-methyl-5, 10-dihydroindeno[1,2-b]indole, and then 100 mL of toluene with vigorous stirring. Methyl iodide (1.8 mL) is then added. The mixture is stirred for three hours at 25° C. and then heated at 100° C. for 30 minutes. After cooling to 25° C., two layers are formed: a pale yellow organic layer and an aqueous layer. They are separated. The precipitate in the organic layer is filtered. The aqueous layer is extracted with toluene, which is then combined with the organic layer, the mixture is then dried over Na2SO4, and filtered. The resulting solution is concentrated till a solid is formed. The solid is isolated from the solution, and combined with the previously collected solid product. The combined solid is washed with ethanol and then with hexane and dried, yielding 3.05 grams of 5,8-dimethyl-5,10-dihydroindeno[1,2-b]indole.

Workup

  1. temperatureheated at 100° C. for 30 minutes
  2. temperatureAfter cooling to 25° C.
  3. customtwo layers are formed
  4. customThey are separated
  5. filtrationThe precipitate in the organic layer is filtered
  6. extractionThe aqueous layer is extracted with toluene, which
  7. dry with materialthe mixture is then dried over Na2SO4
  8. filtrationfiltered
  9. concentrationThe resulting solution is concentrated till a solid
  10. customis formed
  11. customThe solid is isolated from the solution
  12. washThe combined solid is washed with ethanol
  13. dry with materialwith hexane and dried

Sources & evidence

ORD record
ord-a33923f5805746ecaf871ea9c98b5915
Source dataset
uspto-grants-2003_04
Patent number
US06541583B2

Reaction notes

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