Methyl 6-amino-5-nitropyridine-3-carboxylate → Methyl 5,6-diaminopyridine-3-carboxylate

HRID 2120128Notes

Reaction equation

HRID 2120128 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([NH2:13])=[N:6][CH:5]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH2:13])=[N:6][CH:5]=1

Participants

4

Reactant 1

HCID 13768248Methyl 6-amino-5-nitropyridine-3-carboxylate

Product 1

HCID 9920476Methyl 5,6-diaminopyridine-3-carboxylateYield 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 5.97 g (30 mmol) 6-amino-5-nitro-nicotinic acid methyl ester in 30 ml methanol and 600 mg Pd/C (10%) cat was added and hydrogenated at room temperature during 14 h. The catalyst was filtered off and the solution was concentrated to yield 4.74 g (94%) of the title compound as white amorphous solid.

Workup

  1. additionwas added
  2. filtrationThe catalyst was filtered off
  3. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-01b2b74bcddc49c298eceb3157c479f2
Source dataset
uspto-grants-2004_02
Patent number
US06689790B2

Reaction notes

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