1-(2-chloro-5-nitropyridin-4-yl)ethanone → 1-(5-Amino-2-chloro-4-pyridinyl)ethanone

HRID 1028045Notes

Reaction equation

HRID 1028045 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[O:10])[CH3:9])[C:5]([N+:11]([O-])=O)=[CH:4][N:3]=1>C(O)(=O)C.[Fe]>[NH2:11][C:5]1[C:6]([C:8](=[O:10])[CH3:9])=[CH:7][C:2]([Cl:1])=[N:3][CH:4]=1

Participants

4

Reactant 1

HCID 583875681-(2-chloro-5-nitropyridin-4-yl)ethanone

Product 1

HCID 583875841-(5-Amino-2-chloro-4-pyridinyl)ethanoneYield 87%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 1-(2-chloro-5-nitropyridin-4-yl)ethanone (1.0 equiv.) in acetic acid (0.3 M) was added iron (6.0 equiv.). The solution was vigorously stirred for 4 hours, at which time it was filtered through a celite pad (9 cm×3 inches) eluting with MeOH and then ethyl acetate. The volatiles were removed in vacuo, and the crude material was partitioned between ethyl acetate and Na2CO3(sat.). The organic layer was washed further with Na2CO3(sat.) (3×), with NaCl(sat.), dried over MgSO4, filtered and concentrated yielding 1-(5-amino-2-chloropyridin-4-yl)ethanone (87%). LCMS (m/z): 171.0 (MH+); LC Rt=2.20 min. 1H NMR (CDCl3): δ 9.18 (s, 1H), 7.36 (s, 1H), 2.60 (s, 3H).

Workup

  1. filtrationwas filtered through a celite pad (9 cm×3 inches)
  2. washeluting with MeOH
  3. customThe volatiles were removed in vacuo
  4. customthe crude material was partitioned between ethyl acetate and Na2CO3(sat.)
  5. washThe organic layer was washed further with Na2CO3(sat.) (3×), with NaCl(sat.)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-deac81309ebe425ebff1bffdbdef5242
Source dataset
uspto-grants-2014_05
Patent number
US08735424B2

Reaction notes

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