Methanol → Methyl 5-amino-2-methoxypyridine-3-carboxylate

HRID 1290001Notes

Reaction equation

HRID 1290001 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]([N+:13]([O-])=O)=[CH:5][N:4]=1.CO.[H][H]>[OH-].[OH-].[Pd+2].C(Cl)Cl.CO>[CH3:1][O:2][C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]([NH2:13])=[CH:5][N:4]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 14371731Methyl 2-methoxy-5-nitropyridine-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 14371732Methyl 5-amino-2-methoxypyridine-3-carboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

2-Methoxy-3-carbomethoxy-5-nitropyridine (850 mg, 4 mmol) was added to a medium pressure Parr shaker bottle (250 mL) containing 100 mg of 20% Pearlman's catalyst (palladium hydroxide/carbon) and 50 mL of methanol. The bottle was pressurized to 50 psi of hydrogen and shaken for 2 hours. By TLC, no starting material was observed (98/2 CH2Cl2 /MeOH). The catalyst was filtered off, the methanol was removed under reduced pressure and the product used in the next step without further purification. Recovered 680 mg of product (95% yield).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe methanol was removed under reduced pressure
  3. customthe product used in the next step without further purification

Sources & evidence

ORD record
ord-6e3f673ff31645a49e5846b4f8636a48
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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