Potassium Hydroxide → 5,8-Dimethyl-5,6-dihydroindeno[2,1-b]indole

HRID 1868541Notes

Reaction equation

HRID 1868541 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]2[C:11]3[C:16]([C:17](=O)[C:3]1=2)=[CH:15][C:14]([CH3:19])=[CH:13][CH:12]=3.O.NN.[OH-].[K+]>C(O)COCCO.O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]2[C:11]3[C:16]([CH2:17][C:3]1=2)=[CH:15][C:14]([CH3:19])=[CH:13][CH:12]=3

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 113341165,8-dimethylindeno[2,1-b]indol-6(5H)-one

Product 1

HCID 114816975,8-Dimethyl-5,6-dihydroindeno[2,1-b]indole

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1.04 g (0.0042 mol) of 5,8-dimethylindeno[2,1-b]indol-6(5H)-one and 1.12 mL (0.0224 mol) of hydrazine monohydrate in 20 mL of diethylene glycol was stirred at 80° C. for 1 h and then refluxed for 1 h. The resulting mixture was cooled to r.t., treated with a solution of 1.2 g (0.0214 mol) of KOH in 5 mL of water and then it was refluxed for 2 h. The resulting mixture was poured into 100 mL of water, the precipitate was filtered, washed 5 times with 50 mL of water and dried. Yield 0.84 g (86%) of greenish solid.

Workup

  1. temperaturerefluxed for 1 h
  2. temperatureThe resulting mixture was cooled to r.t.
  3. temperatureit was refluxed for 2 h
  4. filtrationthe precipitate was filtered
  5. washwashed 5 times with 50 mL of water
  6. customdried

Sources & evidence

ORD record
ord-cda63983238e4cb5b9288a2f642d95ec
Source dataset
uspto-grants-2009_12
Patent number
US07635781B2

Reaction notes

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