1-(3-nitro-2-pyridinyl)-1H-pyrrole-2-carboxaldehyde → 5,6-Dihydropyrido[3,2-e]pyrrolo[1,2-a]pyrazine

HRID 1290920Notes

Reaction equation

HRID 1290920 reaction equation
[N+:1]([C:4]1[C:5]([N:10]2[CH:14]=[CH:13][CH:12]=[C:11]2[CH:15]=O)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O>C(OCC)(=O)C.[Pd]>[N:6]1[C:5]2[N:10]3[CH:14]=[CH:13][CH:12]=[C:11]3[CH2:15][NH:1][C:4]=2[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 189174681-(3-nitro-2-pyridinyl)-1H-pyrrole-2-carboxaldehyde

Product 1

HCID 189175145,6-Dihydropyrido[3,2-e]pyrrolo[1,2-a]pyrazineYield 134.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 8.0 g of 1-(3-nitro-2-pyridinyl)-1H-pyrrole-2-carboxaldehyde in 150 ml of ethyl acetate is added 800 mg of 10% Pd/C. The mixture is shaken in a Parr hydrogenator for 3 hours and then filtered through diatomaceous earth. The filtrate is concentrated under vacuum to give 8.5 g of solid. The solid is purified by chromatography over silica gel with solvent hexane-ethyl acetate (2:1) as solvent to give 2.6 g of product as white crystals, m.p. 92°-94° C. and 1.6 g of pyrido[3,2-a]pyrrolo[1,2-a]pyrazine as tan needles, m.p. 88° C. to 90° C.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. concentrationThe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-ecc3730839bc4eb99eb3f86115c50e2d
Source dataset
uspto-grants-1998_05
Patent number
US05753648

Reaction notes

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