methyl 6-methoxy-5-nitronicotinate → Methyl 5-amino-6-methoxypyridine-3-carboxylate

HRID 1825392Notes

Reaction equation

HRID 1825392 reaction equation
[CH3:1][O:2][C:3]1[C:12]([N+:13]([O-])=O)=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=1.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:13][C:12]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 2746880methyl 6-methoxy-5-nitronicotinateHCID 178418361HCID 178418361, compound

Product 1

HCID 22145836Methyl 5-amino-6-methoxypyridine-3-carboxylateYield 92.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 6-methoxy-5-nitronicotinate (5.4 g) in ethyl acetate (120 mL) is hydrogenated using 5% palladium on carbon (1 g) as catalyst. When hydrogen uptake ceased the mixture is filtered through a pad of diatomaceous earth and the filtrate evaporated. The residue is triturated with n-pentane and methyl t-butyl ether to give methyl 5-amino-6-methoxynicotinoate (4.3 g) as a light-brown solid, m.p. 108–9° C. [Elemental analysis:—C, 52.99; H, 5.49; N, 15.25%. calculated:—C, 52.74; H, 5.53; N, 15.38%.]

Workup

  1. filtrationis filtered through a pad of diatomaceous earth
  2. customthe filtrate evaporated
  3. customThe residue is triturated with n-pentane and methyl t-butyl ether

Sources & evidence

ORD record
ord-0d902b0b9f5e4804b56cdd570e4bc7dc
Source dataset
uspto-grants-2006_05
Patent number
US07045660B2

Reaction notes

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