Acetic Acid → HCID 22724338, compound

HRID 2086852Notes

Reaction equation

HRID 2086852 reaction equation
[N+:1]([C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[CH2:6][C:7]1[C:12](=[O:13])[N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]2[N:20]=[CH:21][CH:22]=[CH:23][C:9]=2[N:8]=1)([O-])=O.C(O)(=O)C>C(O)C.[Fe]>[NH2:1][C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[CH2:6][C:7]1[C:12](=[O:13])[N:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:10]2[N:20]=[CH:21][CH:22]=[CH:23][C:9]=2[N:8]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 22724421HCID 22724421, compound

Product 1

HCID 22724338HCID 22724338, compoundYield 9.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

The mixture of 2-(2-nitrobenzyl)-3-oxo-4-phenyl-3,4-dihydropyrido[2,3-b]pyrazine (1.39 g), iron (2.17 g) and acetic acid (1.16 g) in ethanol (15 ml) was refluxed for 3 hours. The reaction mixture was cooled and filtered. To the filtrate was added saturated sodium hydrogencarbonate solution, and extracted with ethyl acetate. The organic layer was dried and evaporated. The crude product was purified by silica column chromatography to obtain 2-(2-aminobenzyl)-3-oxo-4-phenyl-3,4-dihydropyrido[2,3-b]pyrazine (120 mg).

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. additionTo the filtrate was added saturated sodium hydrogencarbonate solution
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was dried
  7. customevaporated
  8. customThe crude product was purified by silica column chromatography

Sources & evidence

ORD record
ord-b8601586fe214debb1b5ca4452bcfb10
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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