Methyl 3-methoxy-6-nitro-2-pyrazinecarboxylate → Methyl 6-amino-3-methoxy-2-pyrazinecarboxylate

HRID 392329

Reaction equation

HRID 392329 reaction equation
[H][H].[CH3:3][O:4][C:5]1[C:6]([C:14]([O:16][CH3:17])=[O:15])=[N:7][C:8]([N+:11]([O-])=O)=[CH:9][N:10]=1>C(=O)([O-])[O-].[Ca+2].[Pd+2].C(=O)([O-])[O-].C(O)(=O)C>[NH2:11][C:8]1[N:7]=[C:6]([C:14]([O:16][CH3:17])=[O:15])[C:5]([O:4][CH3:3])=[N:10][CH:9]=1

Participants

5

Reactant 2

HCID 22662794Methyl 3-methoxy-6-nitro-2-pyrazinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 22662843Methyl 6-amino-3-methoxy-2-pyrazinecarboxylateYield 71.8%

Reagents, catalysts & solvents 2

HCID 17803853Palladium on calcium carbonateCatalystHCID 176Acetic AcidSolvent

Procedure

At room temperature and under a pressure of 1 atmosphere, hydrogen gas was introduced into a mixture of 24.3 g of methyl 3-methoxy-6-nitro-2-pyrazinecarboxylate, 480 mL of acetic acid and 1.2 g of lead-poisoned palladium-calcium carbonate until the mixture became showing no further absorption of hydrogen. After filtering off insoluble matter from the reaction mixture, the solvent was removed under reduced pressure, and the solid product thus obtained was washed with ethyl acetate and diethyl ether. Thus, 15.0 g of methyl 6-amino-3-metoxy-2-pyrazinecarboxylate was obtained as a solid product. Furthermore, the solvent was removed from the filtrate under reduced pressure to obtain a solid product, and the solid product was washed with ethyl acetate to obtain 2.3 g of methyl 6-amino-3-methoxy-2-pyrazinecarboxylate as a solid product.

Workup

  1. customno further absorption of hydrogen
  2. filtrationAfter filtering off insoluble matter from the reaction mixture
  3. customthe solvent was removed under reduced pressure
  4. customthe solid product thus obtained
  5. washwas washed with ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-d607e4676fc845f4bdd82f325eb24bc2
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Linked notes

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