Ethenamine, N,N-dimethyl-2-nitro- → (E)-5-Chloro-2-ethyl-3-(2-nitroethenyl)-1H-indole

HRID 11399

Reaction equation

HRID 11399 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][CH3:12])=[CH:5]2.CN(C)[CH:15]=[CH:16][N+:17]([O-:19])=[O:18]>FC(F)(F)C(O)=O.CCOC(C)=O.CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][CH3:12])=[C:5]2/[CH:15]=[CH:16]/[N+:17]([O-:19])=[O:18]

Participants

5

Reactant 2

HCID 518458Ethenamine, N,N-dimethyl-2-nitro-HCID 205171755-chloro-2-ethyl-1H-indole

Product 1

HCID 21974279(E)-5-Chloro-2-ethyl-3-(2-nitroethenyl)-1H-indole

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 21584169Diethylether ethylacetateSolvent

Procedure

The indole 3 (5 mmol) was added to a stirred ice-cooled solution of 1-(dimethylamino)-2-nitroethylene (0.58 g, 5 mmol) in trifluoroacetic acid (5 mL). The mixture was stirred at room temperature under N2, for 0.5 h and then poured onto ice water. The aqueous solution was extracted with ethyl acetate, the combined organic layers were washed with a saturated NaHCO3 solution and then with water. After drying over Na2SO4, the solvent was evaporated under reduced pressure to give a crude orange solid which was suspended in a mixture of EtOAc-Et2O and filtered, or chromatographed on silica gel (cyclohexane/EtOAc, 1:1, as eluent).

Workup

  1. additionpoured onto ice water
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. washthe combined organic layers were washed with a saturated NaHCO3 solution
  4. dry with materialAfter drying over Na2SO4
  5. customthe solvent was evaporated under reduced pressure
  6. customto give a crude orange solid which
  7. filtrationfiltered
  8. customchromatographed on silica gel (cyclohexane/EtOAc, 1:1, as eluent)

Sources & evidence

ORD record
ord-fd5736776b90490195ef7a703ff54b79
Source dataset
uspto-grants-2006_08
Patent number
US07098233B2

Linked notes

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