Hydrochloric Acid → 8-Methyl-5,10-dihydroindeno[1,2-b]indole

HRID 1264125Notes

Reaction equation

HRID 1264125 reaction equation
Cl.[C:2]1(=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.Cl.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20]N)=[CH:16][CH:15]=1>C(O)C>[CH3:13][C:14]1[CH:19]=[CH:18][C:17]2[NH:20][C:2]3[C:10]4[C:5]([CH2:4][C:3]=3[C:16]=2[CH:15]=1)=[CH:6][CH:7]=[CH:8][CH:9]=4

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 67351-IndanoneHCID 125044-Methylphenylhydrazine monohydrochloride

Product 1

HCID 222470798-Methyl-5,10-dihydroindeno[1,2-b]indoleYield 91.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

In a 250 mL round bottom flask, 180 mL of ethanol, 10 mL of HCl, 16.3 grams of 1-indanone (0.124 mole) and 19.5 grams of p-methylphenylhydrazine hydrochloride (0.124 mole) are heated to reflux for six hours. After cooling to 25° C., the resulting precipitate is filtered, washed twice with 100 mL of 10% aqueous ethanol, twice with 50 mL of water, and then twice with 50 mL of hexane. After drying, 25 grams of 8-methyl-5, 10-dihydroindeno[1,2-b]indole is obtained.

Workup

  1. temperatureto reflux for six hours
  2. filtrationthe resulting precipitate is filtered
  3. washwashed twice with 100 mL of 10% aqueous ethanol, twice with 50 mL of water
  4. customAfter drying

Sources & evidence

ORD record
ord-2d127d65184a454bb04ee95ebfc3b53d
Source dataset
uspto-grants-2003_04
Patent number
US06541583B2

Reaction notes

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