Ammonium Chloride → HCID 15082749, compound

HRID 439857Notes

Reaction equation

HRID 439857 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]=[C:6]3[C:11]4[C:16]([CH2:17][C:5]3([CH3:18])[C:4]=2[CH:3]=1)=[CH:15][CH:14]=[CH:13][CH:12]=4.[CH3:19][Li].[Cl-].[NH4+]>O1CCCC1.C(OCC)C>[CH3:19][C@@:6]12[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:17][C@:5]1([CH3:18])[C:4]1[CH:3]=[C:2]([CH3:1])[CH:10]=[CH:9][C:8]=1[NH:7]2

Participants

6

Reactant 3

HCID 25517Ammonium Chloride2×HCID 22408447HCID 22408447, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 15082749HCID 15082749, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 9b,10-dihydro-8,9b-dimethylindeno[1,2-b]indole, (5.05 g, 0.022 mol) in dry tetrahydrofuran (100 cm3) at -78° C., under nitrogen, in a flame dried flask, was added dropwise methyllithium, (1.4M solution in diethyl ether, 23.2 cm3, 0.032 mol). The mixture was stirred at -78° C. for 2 hours and then at -15° C. for a further 1 hour. Saturated ammonium chloride solution (3 cm ) was then added and the mixture allowed to warm to room temperature. The reaction mixture was portioned between ether and saturated ammonium chloride solution and the layers separated. The aqueous phase was extracted with diethyl ether (2×25 cm3) and the combined organic extracts were washed with brine, dried (Na2SO4) and evaporated to afford the title compound as an off white solid. This was purified by flash chromatography on silica gel eluting with 3-10% ethyl acetate/60°-80° petrol to yield a colourless solid. Yield: 2.73 g, 51% .M.p. 208°-212° C. 1H NMR (CDCl3) δ: 7.1-7.3 (4H, m), 6.94 (1H, m), 6.77 (1H, d, J=7.8 Hz), 6.46 (1H, d, J=7.8 Hz), 3.35 (1H, d, J=15.9 Hz), 3.06 (1H, d, J=15.9 Hz), 2.22 (3H, s), 1.46 (3H, s), 1.34 (3H, s).

Workup

  1. waitat -15° C. for a further 1 hour
  2. temperatureto warm to room temperature
  3. customthe layers separated
  4. extractionThe aqueous phase was extracted with diethyl ether (2×25 cm3)
  5. washthe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-80900bba775c4d0cbe4e7fae9b7cdd41
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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