1-(2-nitrophenyl)-1H-pyrrole-2-carbaldehyde → 4,5-Dihydropyrrolo[1,2-a]quinoxaline

HRID 3495

Reaction equation

HRID 3495 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]=O)([O-])=O>C(O)C.C(OCC)(=O)C.[Pd]>[CH:14]1[N:10]2[C:5]3[C:4]([NH:1][CH2:15][C:11]2=[CH:12][CH:13]=1)=[CH:9][CH:8]=[CH:7][CH:6]=3

Participants

5

Reactant 1

HCID 47153911-(2-nitrophenyl)-1H-pyrrole-2-carbaldehyde

Product 1

HCID 118051814,5-Dihydropyrrolo[1,2-a]quinoxalineYield 44.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.0 g of 1-(2-nitrophenyl)-1H-pyrrole-2-carboxaldehyde in 40 ml of ethyl alcohol and 40 ml of ethyl acetate, under argon, is added 40 mg of 10% Pd/C. The mixture is hydrogenated at 40 psi for 2 hours and filtered through diatomaceous earth. The filtrate is concentrated in vacuo to a residue which is dissolved in ether and treated with hexanes to give 0.35 g of the desired product as a beige solid m.p. 108°-110° C.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. concentrationThe filtrate is concentrated in vacuo to a residue which
  3. dissolutionis dissolved in ether
  4. additiontreated with hexanes

Sources & evidence

ORD record
ord-f2ec50dbf2f74eb09d479fedd495864b
Source dataset
uspto-grants-1998_03
Patent number
US05733905

Linked notes

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