2-Methyl-2-(6-nitropyridin-3-yl)-propionic acid methyl ester → Methyl 2-(6-aminopyridin-3-yl)-2-methylpropanoate

HRID 2069721Notes

Reaction equation

HRID 2069721 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]([CH3:15])([C:6]1[CH:7]=[N:8][C:9]([N+:12]([O-])=O)=[CH:10][CH:11]=1)[CH3:5].[H][H]>C1COCC1.[Pd]>[CH3:1][O:2][C:3](=[O:16])[C:4]([C:6]1[CH:7]=[N:8][C:9]([NH2:12])=[CH:10][CH:11]=1)([CH3:15])[CH3:5]

Participants

5

Reactant 2

HCID 594738022-Methyl-2-(6-nitropyridin-3-yl)-propionic acid methyl esterHCID 178418361HCID 178418361, compound2×

Product 1

HCID 21998700Methyl 2-(6-aminopyridin-3-yl)-2-methylpropanoateYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

2-Methyl-2-(6-nitropyridin-3-yl)-propionic acid methyl ester (1.88 g, 8.4 mmol) was dissolved in THF and 200 mg of 10% palladium on carbon was added. The reaction was exposed to hydrogen at a pressure of 50 psi for 5 hrs. NMR showed the reduction was incomplete. More palladium on carbon was added and the reaction was exposed to hydrogen again at 50 psi for several hrs. The reaction was filtered through celite and concentrated to give 1.5 g (92%) of 2-(6-amino-pyridin-3-yl)-2-methyl-propionic acid methyl ester which was used without purification.

Workup

  1. filtrationThe reaction was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-2399ea306bdb4a618dbc8232adcae82c
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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