Triethylamine → 5-(2,6-Dimethoxybenzoyl)-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoxaline

HRID 543550Notes

Reaction equation

HRID 543550 reaction equation
[CH2:1]1[N:5]2[C:6]3[C:11]([NH:12][CH2:13][CH:4]2[CH2:3][CH2:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3.C(N(CC)CC)C.[CH3:21][O:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[C:24]=1[C:25](Cl)=[O:26]>CC(C)=O>[CH3:33][O:32][C:28]1[CH:29]=[CH:30][CH:31]=[C:23]([O:22][CH3:21])[C:24]=1[C:25]([N:12]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]2[CH2:1][CH2:2][CH2:3][CH:4]2[CH2:13]1)=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 748102,6-Dimethoxybenzoyl chlorideHCID 134137861H,2H,3H,3aH,4H,5H-pyrrolo(1,2-a)quinoxaline

Product 1

HCID 133420925-(2,6-Dimethoxybenzoyl)-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoxalineYield 79%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of the 1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoxaline 1.7 g. (0.009 mole) and 4 ml. of dry triethylamine in 50 ml. of dry acetone was added 2.5 g. (0.01 mole) of 2,6-dimethoxybenzoyl chloride. The reaction mixture was stirred for three hours and filtered, and the acetone was evaporated under vacuo. The residue was washed with water, dried and recrystallized from aqueous ethanol to afford 2.4 g. (79% yield) of the title compound, m.p. 140°-142° C.

Workup

  1. filtrationfiltered
  2. customthe acetone was evaporated under vacuo
  3. washThe residue was washed with water
  4. customdried
  5. customrecrystallized from aqueous ethanol
  6. customto afford 2.4 g

Sources & evidence

ORD record
ord-2ecf357cce19477e95c3c4e864e315b8
Source dataset
uspto-grants-1984_05
Patent number
US04446323

Reaction notes

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