Methyl 5-nitropicolinate → Methyl 5-aminopyridine-2-carboxylate

HRID 2291788Notes

Reaction equation

HRID 2291788 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([O:12][CH3:13])=[O:11])=[N:8][CH:9]=1)([O-])=O.[H][H]>C(OCC)(=O)C.[Pt]=O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]([O:12][CH3:13])=[O:11])=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 12457882Methyl 5-nitropicolinateHCID 178418361HCID 178418361, compound

Product 1

HCID 12457877Methyl 5-aminopyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution containing 10 g methyl 5-nitropicolinate in 400 ml ethyl acetate is stirred under hydrogen in the presence of 1 g platinum oxide at room temperature and atmospheric pressure. When no further hydrogen uptake occurs, the catalyst is removed by filtration, the filtrate concentrated, and the product collected. This is recrystallized from ethyl acetate to give analytically pure methyl 5-aminopicolinate, mp 147°-150.5° C.

Workup

  1. customthe catalyst is removed by filtration
  2. concentrationthe filtrate concentrated
  3. customthe product collected
  4. customThis is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-94af8a3e43d94bffbffcb6ed66def48f
Source dataset
uspto-grants-1989_01
Patent number
US04798619

Reaction notes

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