Ethyl 2-(6-methyl-5-nitropyridin-2-YL)acetate → Ethyl 2-(5-amino-6-methyl-2-pyridinyl)acetate

HRID 1502125Notes

Reaction equation

HRID 1502125 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:4][C:3]=1[N+:14]([O-])=O.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:14][C:3]1[CH:4]=[CH:5][C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:7][C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 53419421Ethyl 2-(6-methyl-5-nitropyridin-2-YL)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 89619013Ethyl 2-(5-amino-6-methyl-2-pyridinyl)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 2-(6-methyl-5-nitropyridin-2-yl)acetate (1.10 g, 4.91 mmol) was dissolved in ethyl acetate and added Pd/C (0.5 g) then stirred under a balloon of hydrogen for 2 hrs. Filtered over catalyst and concentrated to yield ethyl 2-(5-amino-6-methylpyridin-2-yl)acetate: LC-MS: M+1=195;

Workup

  1. filtrationFiltered over catalyst
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-87e45446156942d5bebbfb531899a8d7
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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