Hydrochloric Acid → 9b,10-Dihydro-9b-methyl-8-isopropylindeno-[1,2-b]indole

HRID 439865Notes

Reaction equation

HRID 439865 reaction equation
Cl.[CH:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11]N)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[CH3:13][CH:14]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=O.Cl>C(O)C>[CH3:13][C:14]12[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]1=[N:11][C:8]1[CH:7]=[CH:6][C:5]([CH:2]([CH3:4])[CH3:3])=[CH:10][C:9]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2492622-MethylindanoneHCID 2733248[4-(Propan-2-yl)phenyl]hydrazine hydrochloride

Product 1

HCID 150827489b,10-Dihydro-9b-methyl-8-isopropylindeno-[1,2-b]indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-isopropylphenylhydrazine hydrochloride, (6.50 g, 0.035 mmol) in absolute ethanol (140 cm3) was added dropwise 2-methyl-1-indanone, (4.6 g, 0.032 mmol) followed by conc. hydrochloric acid (2.5 cm3). The mixture was refluxed for 2 hours and the ethanol evaporated. The residue was portioned between diethyl ether (100 cm3) and water (100 cm3) and the layers separated. The aqueous phase was extracted with diethyl ether (2×30 cm3) and the organic extracts were washed sequentially with saturated sodium bicarbonate solution and brine, and then dried (Na2SO4). Removal of the solvent gave the title compound which was purified by flash chromatography on silica gel eluting with 10% ethyl acetate/60°-80° petrol, to yield a yellow gum; (1.62 g, 25%); 1H NMR (CDCl3) δ: 7.88 (1H, m), 7.55 (1H, d, J=8.1 Hz) 7.41 (3H, m) 7.30 (1H, d, J=1.8 Hz) 7.23 (1H, dd, J=1.8 Hz and 7.1 Hz) 3.10 (1H, d, J=14.7 Hz) 2.98 (1H, septet, J=7.0 Hz) 2.85 (1H, d, J=14.7 Hz) 1.39 (3H, s) 1.30 (6H, d, J=7.0 Hz).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. customthe ethanol evaporated
  3. customthe layers separated
  4. extractionThe aqueous phase was extracted with diethyl ether (2×30 cm3)
  5. washthe organic extracts were washed sequentially with saturated sodium bicarbonate solution and brine
  6. dry with materialdried (Na2SO4)
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-8632e993d3cb42898d5589c2c4a8a0ff
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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