Water → N-methyl-5,10-dihydroindeno[1,2-b]indole

HRID 2081675Notes

Reaction equation

HRID 2081675 reaction equation
[H-].[Na+].[CH:3]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:4]=1[CH2:5][C:6]1[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8][C:7]=12.S(OC)(O[CH3:23])(=O)=O.O>CS(C)=O>[CH3:23][N:8]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=2[C:6]2[CH2:5][C:4]3[C:15]([C:7]1=2)=[CH:16][CH:17]=[CH:18][CH:3]=3

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 975985,10-Dihydroindeno[1,2-b]indole

Product 1

HCID 7103144N-methyl-5,10-dihydroindeno[1,2-b]indole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
70 °C

Procedure

Sodium hydride (375 mq, 15.6 mmol) was added to dimethylsulfoxide (DMSO) (13 cm3) under an atmosphere of nitrogen. The solution was then heated to 70° C. until no more gas (H2) evolved. The solution was cooled to room temperature and 5,10-dihydroindeno[1,2-b]indole (2.69 g, 13.1 mmol) dissolved in a minimum amount of DMSO was added. After stirring at room temperature for 1 hour, dimethyl sulphate (1.5 cm3, 15 mmol) was introduced, and stirring continued for a further 1 hour. Water (3 cm3) was cautiously added, and the reaction then poured into ice/water. The solid thus formed was collected by suction filtration, washed firstly with water, dried on the water pump, and then washed with petrol (60°-80° C.). Crystallization from ethanol yielded colourless needles of the title compound. Yield: 1.52 g (53%). M.p. 152° C. 1H NMR (CDCl3) δ: 3.55 (2H, s,), 3.85 (3H, s,), 6.8-7.4 (8H, m, arom.).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. additionwas added
  3. stirringstirring
  4. waitcontinued for a further 1 hour
  5. customthe reaction
  6. customThe solid thus formed
  7. filtrationwas collected by suction filtration
  8. washwashed firstly with water
  9. dry with materialdried on the water pump
  10. washwashed with petrol (60°-80° C.)
  11. customCrystallization from ethanol yielded colourless needles of the title compound

Sources & evidence

ORD record
ord-85f1431771ce4b4290c97f29c8d58d29
Source dataset
uspto-grants-1993_02
Patent number
US05185360

Reaction notes

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