Water → 2,5-Dimethyl-5,6-dihydroindeno[2,1-b]indole

HRID 1280333Notes

Reaction equation

HRID 1280333 reaction equation
[OH-].[Na+].O.[CH3:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]1[CH2:14][C:15]3[C:20]([C:8]2=1)=[CH:19][CH:18]=[CH:17][CH:16]=3.[CH3:21]I>C1C=CC=CC=1>[CH3:21][N:10]1[C:11]2[C:7](=[CH:6][C:5]([CH3:4])=[CH:13][CH:12]=2)[C:8]2[C:20]3[C:15]([CH2:14][C:9]1=2)=[CH:16][CH:17]=[CH:18][CH:19]=3

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 155337282-Methyl-5,6-dihydroindeno[2,1-b]indole

Product 1

HCID 155337292,5-Dimethyl-5,6-dihydroindeno[2,1-b]indoleYield 88%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

45 g of NaOH, 60 ml of water, 60 ml of benzene, 0.3 g of trimethyl-cethyl-ammonium bromide, 19.3(0.088 mol) of 2-methyl-5,6-dihydroindeno[2,1-b]indole, prepared in Example 8-bis, and 7.5 ml (0.12 mol) of CH3I were placed in a bulb. The resulting two-phase system was stirred for 2 hours at room temperature and then 10 minutes at reflux. Then the reaction mixture cooled to room temperature and filtered. The obtained precipitate was washed twice with ethanol and finally dried, thus obtaining 18 g of N-methyl-2-methyl-5,6-dihydroindeno[2,1-b]indole (yield=88%).

Workup

  1. temperature10 minutes at reflux
  2. temperatureThen the reaction mixture cooled to room temperature
  3. filtrationfiltered
  4. washThe obtained precipitate was washed twice with ethanol
  5. customfinally dried

Sources & evidence

ORD record
ord-5472da883c5a4b4c8b220d24b7c9823f
Source dataset
uspto-grants-2002_09
Patent number
US06451724B1

Reaction notes

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