Potassium Hydroxide → 2-methyl-8H-indeno[2,1-b]thiophene

HRID 1868538Notes

Reaction equation

HRID 1868538 reaction equation
[CH3:1][C:2]1[S:6][C:5]2[C:7](=O)[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:4]=2[CH:3]=1.O.NN.[OH-].[K+]>C(O)COCCO.O>[CH3:1][C:2]1[S:6][C:5]2[CH2:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 112756712-methyl-8H-indeno[2,1-b]thiophen-8-one

Product 1

HCID 113213872-methyl-8H-indeno[2,1-b]thiophene

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6.83 g (0.034 mol) of 2-methyl-8H-indeno[2,1-b]thiophen-8-one and 9.1 mL (0.182 mol) of hydrazine monohydrate in 91 mL of diethylene glycol was stirred at 80° C. for 40 min and then refluxed for 1 h. The resulting mixture was cooled to room temperature, treated with a solution of 9.5 g (0.169 mol) of KOH in 34 mL water and then refluxed for 2 h. The resulting mixture was poured into 600 mL of water, the precipitate was filtered, washed 5 times with 200 mL of water and dried. Yield 5.8 g (92%).

Workup

  1. temperaturerefluxed for 1 h
  2. temperatureThe resulting mixture was cooled to room temperature
  3. temperaturerefluxed for 2 h
  4. filtrationthe precipitate was filtered
  5. washwashed 5 times with 200 mL of water
  6. customdried

Sources & evidence

ORD record
ord-7330e21cf03146989d0f1f7327e1c232
Source dataset
uspto-grants-2009_12
Patent number
US07635781B2

Reaction notes

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