Triethylamine → HCID 21474180, compound

HRID 2294165Notes

Reaction equation

HRID 2294165 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.Cl[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=1[N+:20]([O-:22])=[O:21].C(N(CC)CC)C>C(O)C>[C:16]([C:15]1[CH:18]=[CH:19][C:12]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)=[C:13]([N+:20]([O-:22])=[O:21])[CH:14]=1)#[N:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13655Benzonitrile, 4-chloro-3-nitro-HCID 788675-Aminoindole

Product 1

HCID 21474180HCID 21474180, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Aminoindole (0.264 g, 2.00 mmoles) and 4-chloro-3-nitrobenzonitrile (0.444 g, 3.00 mmoles) were combined with triethylamine (0.42 ml, 3.01 mmoles) in absolute ethanol and the reaction was heated at reflux under nitrogen for 3 hours. After evaporation of the solvent, the residue was chromatographed using ether/hexanes [1:1] to afford the title compound (79%) as a red amorphous solid. Mp, decomposes 134° C.; 13C NMR (DMSO-d6) δ146.9, 137.3, 134.8, 131.9, 131.3, 128.9, 128.3, 126.9, 119.8, 118.2, 117.9, 117.2, 112.5, 101.5, 97.4; LRMS (m/z, relative intensity) 278 (M+, 100), 261 (31), 244 (73), 231 (78). HRMS calculated for C15H10N4O2 : 278.0802. Found: 278.0808. Analytical calculated for C15H10N4O2 : C, 64.74; H, 3.62; N, 20.13. Found: 64.84; H, 3.57; N, 20.13.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux under nitrogen for 3 hours
  3. customAfter evaporation of the solvent
  4. customthe residue was chromatographed

Sources & evidence

ORD record
ord-f2b4cfbce0594d3b87c77b0e8b93c01c
Source dataset
uspto-grants-1997_11
Patent number
US05688809

Reaction notes

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