diethyl 5-nitropyridine-2,3-dicarboxylate-N-oxide → Diethyl 5-aminopyridine-2,3-dicarboxylate

HRID 1898790Notes

Reaction equation

HRID 1898790 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N+:8]([O-])[CH:9]=1)([O-])=O>C(O)(=O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:8][CH:9]=1

Participants

4

Reactant 1

HCID 15451775diethyl 5-nitropyridine-2,3-dicarboxylate-N-oxide

Product 1

HCID 15451783Diethyl 5-aminopyridine-2,3-dicarboxylate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Procedure

17 g (0.060 mol) of diethyl 5-nitropyridine-2,3-dicarboxylate-N-oxide in 200 ml of glacial acetic acid were added to a mixture of 10.7 g (0.19 mol) of iron powder in 50 ml of glacial acetic acid at 70° C. with stirring in the course of 20 minutes. After stirring at 70° C. for 1 hour, the reaction mixture was cooled, and the precipitate was filtered off with suction and washed with ethyl acetate. The filtrate was concentrated under reduced pressure, dissolved in methylene chloride, washed with water and with saturated sodium chloride solution, dried over magnesium sulfate and filtered off with suction through silica gel. After concentrating under reduced pressure, 11 g (77% of theory) of the title compound were obtained as a semisolid mass.

Workup

  1. stirringAfter stirring at 70° C. for 1 hour
  2. temperaturethe reaction mixture was cooled
  3. filtrationthe precipitate was filtered off with suction
  4. washwashed with ethyl acetate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. dissolutiondissolved in methylene chloride
  7. washwashed with water and with saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered off with suction through silica gel
  10. concentrationAfter concentrating under reduced pressure, 11 g (77% of theory) of the title compound
  11. customwere obtained as a semisolid mass

Sources & evidence

ORD record
ord-0e3d6c0347db45f0b628b7e9a3fbb760
Source dataset
uspto-grants-1996_11
Patent number
US05571774

Reaction notes

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