Ethyl 2-(3-nitropyridin-4-yl)acetate → Ethyl (3-aminopyridin-4-yl)acetate

HRID 840931Notes

Reaction equation

HRID 840931 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[N+:12]([O-])=O)[CH3:2]>[Pd].C(O)C>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[NH2:12])[CH3:2]

Participants

4

Reactant 1

HCID 12407500Ethyl 2-(3-nitropyridin-4-yl)acetate

Product 1

HCID 12407502Ethyl (3-aminopyridin-4-yl)acetateYield 111.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a 250-ml Parr flask was added 0.30 g (1.4 mmol) of 3-nitro-4-pyridineacetic acid ethyl ester, 50 mg of 10% palladium on charcoal and 100 mL of ethanol. The mixture was subjected to hydrogenation using a Parr hydrogenator at 40 PSI for 15 min. The mixture was filtered through celite, and the filtrate was concentrated to give an oil which crystallised under a high vacuum to afford 0.282 g of the title compound as a yellow solid. 1H NMR (DMSO-d6): δ1.15 (t, J=7.2 Hz, 3H), 3.52 (s, 2H), 4.05 (q, J=7.2 Hz, 2H), 5.11 (s, 2H), 6.89 (d, J=4.8 Hz, 1H), 7.67 (d, J=4.8 Hz, 1H), 7.92 (s, 1H).

Workup

  1. customfor 15 min
  2. filtrationThe mixture was filtered through celite
  3. concentrationthe filtrate was concentrated
  4. customto give an oil which
  5. customcrystallised under a high vacuum

Sources & evidence

ORD record
ord-3f47181f6a3f47039b7ca4681bf61e54
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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