Acetic Acid → HCID 22724338, compound

HRID 2231028Notes

Reaction equation

HRID 2231028 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-d5d5edbbd61c498c94361569ab622641
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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