2-Indanone → Indole

HRID 2081678Notes

Reaction equation

HRID 2081678 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)C[C:2]1=O.Cl.C1([NH:18]N)C=CC=CC=1>C(O)(=O)C>[NH:18]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:1]=[CH:2]1

Participants

4

Reactant 2

HCID 119832-IndanoneHCID 60962Phenylhydrazine hydrochloride

Product 1

HCID 798Indole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Indanone (5.25 g, 39.7 mmol) and phenylhydrazine hydrochloride (5.74 g, 39.7 mmol), were heated to reflux in glacial acetic acid (60 cm3) for 1 hour, and then cooled. The solution was poured into ice/water, and the solid precipitate collected by filtration. After partial purification by column chromatography, and crystallization (charcoal) from ethyl acetate to yielded colourless needles of the title compound. Yield 0.64 g (80%). M.p. 205° C. 1H NMR (DMSO-d6) δ: 3.65 (2H, s,), 7.0-7.2 (8H,), 10.40 (1H, br,).

Workup

  1. temperaturecooled
  2. filtrationthe solid precipitate collected by filtration
  3. customAfter partial purification
  4. customby column chromatography, and crystallization (charcoal) from ethyl acetate

Sources & evidence

ORD record
ord-5ca2b742c9304f4db0278748b3b8b71e
Source dataset
uspto-grants-1993_02
Patent number
US05185360

Reaction notes

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