Methyl 6-(methylamino)-5-nitronicotinate → Methyl 5-amino-6-(methylamino)pyridine-3-carboxylate

HRID 50190Notes

Reaction equation

HRID 50190 reaction equation
[CH3:1][NH: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.C(O)C.N>C(O)C.ClCCl.[Pd]>[NH2:13][C:12]1[C:3]([NH:2][CH3:1])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 3

HCID 18412421Methyl 6-(methylamino)-5-nitronicotinateHCID 86587043Ethyl acetate ethanol ammoniaHCID 178418361HCID 178418361, compound

Product 1

HCID 18412673Methyl 5-amino-6-(methylamino)pyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584144Dichloromethane ethanolSolvent

Procedure

To a solution of 3.1 g (15 mmol) of methyl 6-methylamino-5-nitronicotinate in 100 mL of ethanol/dichloromethane (3:1) was added 1 g of palladium on charcoal (10%) and the resulting suspension was hydrogenated at room temperature under 5 bar of hydrogen pressure for 1.5 hours. The catalyst was then filtered off and the solvent was distilled off in vacuo. The crude oily product obtained was further reacted directly. Yield: 2.4 g (92% of theory); Rf value: 0.44 (silica gel; ethyl acetate/ethanol/ammonia=90:10:1).

Workup

  1. filtrationThe catalyst was then filtered off
  2. distillationthe solvent was distilled off in vacuo
  3. customThe crude oily product obtained
  4. customwas further reacted directly

Sources & evidence

ORD record
ord-33fe644023524c8aa8fe79dfb685ac47
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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