Triethylamine → 4,5-Dihydro-5-(4-nitrobenzoyl)pyrrolo[1,2-a]quinoxaline

HRID 1739886Notes

Reaction equation

HRID 1739886 reaction equation
[CH:1]1[N:5]2[C:6]3[C:11]([NH:12][CH2:13][C:4]2=[CH:3][CH:2]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3.C(N(CC)CC)C.[N+:21]([C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1)([O-:23])=[O:22]>C(Cl)Cl.C(OCC)(=O)C>[N+:21]([C:24]1[CH:25]=[CH:26][C:27]([C:28]([N:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]3[CH:1]=[CH:2][CH:3]=[C:4]3[CH2:13]2)=[O:29])=[CH:31][CH:32]=1)([O-:23])=[O:22]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 118051814,5-Dihydropyrrolo[1,2-a]quinoxaline

Product 1

HCID 218371354,5-Dihydro-5-(4-nitrobenzoyl)pyrrolo[1,2-a]quinoxaline

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5 mmol of 4,5-dihydro-pyrrolo-[1,2-a]quinoxaline in 50 ml of methylene chloride under argon is added 10 mmol of triethylamine followed by ice bath cooling. A solution of 5 mmol of 4-nitrobenzoyl chloride in 10 ml of methylene chloride is added dropwise. Following complete addition, the ice bath is removed and the reaction mixture stirred at room temperature for 2 hours. The volatiles are removed in vacuo to give a residue which is dissolved in ethyl acetate. The solution is washed with water, 1 N HCl, NaHCO3, and brine. The reaction mixture is dried with Na2SO4, filtered and evaporated in vacuo to give a solid which is purified by flash chromatography to give the desired product (from ethyl acetate) as a solid, m.p. 174-178° C.

Workup

  1. customfollowed by ice bath
  2. temperaturecooling
  3. additionaddition
  4. customthe ice bath is removed
  5. customThe volatiles are removed in vacuo
  6. customto give a residue which
  7. washThe solution is washed with water, 1 N HCl, NaHCO3, and brine
  8. dry with materialThe reaction mixture is dried with Na2SO4
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customto give a solid which
  12. customis purified by flash chromatography

Sources & evidence

ORD record
ord-4b555078c4e74eb9a1ee90202baf39cb
Source dataset
uspto-grants-1999_10
Patent number
US05968937

Reaction notes

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