2-Indanone → Indeno[2,1-b]indole

HRID 1759681Notes

Reaction equation

HRID 1759681 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=O.Cl.[C:12]1(C)[CH:17]=[CH:16][C:15]([NH:18]N)=[CH:14][CH:13]=1>C(O)(=O)C>[CH:13]1[CH:12]=[CH:17][CH:16]=[C:15]2[C:14]=1[C:1]1[C:2]([CH:3]=[C:4]3[C:9]=1[CH:8]=[CH:7][CH:6]=[CH:5]3)=[N:18]2

Participants

4

Reactant 2

HCID 119832-IndanoneHCID 125044-Methylphenylhydrazine monohydrochloride

Product 1

HCID 18445982Indeno[2,1-b]indole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-indanone (51.0 g, 0.39 mol) and p-tolylhydrazine hydrochloride (61.4 g, 0.39 mol) is dissolved in glacial acetic acid (525 mL) and is vigorously stirred and heated to reflux. The mixture turns red and is heated for 2 h. After cooling to room temperature, it is poured into ice water (1 L). The precipitate is filtered to afford a solid, which is washed with water (about 1 L). The solid is dissolved in ethyl acetate (1.4 L), activated charcoal is added, and the mixture is gently warmed. The mixture is then cooled and filtered over a pad of Celite. The filtrate is dried over Na2SO4 filtered, and is then concentrated to 450 mL and cooled to −30° C. for 3 days. The crystalline solid is filtered and washed with chilled (−78° C.) hexanes (2×500 mL). The beige solid is collected and dried under vacuum (47.1 g, 56%).

Workup

  1. temperatureheated to reflux
  2. temperatureis heated for 2 h
  3. filtrationThe precipitate is filtered
  4. customto afford a solid, which
  5. washis washed with water (about 1 L)
  6. dissolutionThe solid is dissolved in ethyl acetate (1.4 L)
  7. additionactivated charcoal is added
  8. temperaturethe mixture is gently warmed
  9. temperatureThe mixture is then cooled
  10. filtrationfiltered over a pad of Celite
  11. dry with materialThe filtrate is dried over Na2SO4
  12. filtrationfiltered
  13. concentrationis then concentrated to 450 mL
  14. temperaturecooled to −30° C. for 3 days
  15. filtrationThe crystalline solid is filtered
  16. washwashed
  17. temperaturewith chilled (−78° C.) hexanes (2×500 mL)
  18. customThe beige solid is collected
  19. customdried under vacuum (47.1 g, 56%)

Sources & evidence

ORD record
ord-8a170ad3a7b94839ad12ca2cffd2f0d2
Source dataset
uspto-grants-2005_01
Patent number
US06838410B2

Reaction notes

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