4-Cyclohexenyl-3-nitropyridine → 4-Cyclohexenylpyridin-3-amine

HRID 69875Notes

Reaction equation

HRID 69875 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[N+:13]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1>C(O)(=O)C.[Fe]>[C:1]1([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[NH2:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

4

Reactant 1

HCID 690448894-Cyclohexenyl-3-nitropyridine

Product 1

HCID 690422534-Cyclohexenylpyridin-3-amineYield 99%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A heterogeneous solution of 4-cyclohexenyl-3-nitropyridine (1.0 eq.) and iron (6.0 eq) in acetic acid, at a concentration of 0.4 M, was stirred vigorously for 2 hours. The mixture was then passed through a celite pad, eluting with MeOH. Upon removal of the volatiles in vacuo, the residue was dissolved in EtOAc, washed with Na2CO3(sat.), NaCl(sat.), was dried over MgSO4, was filtered and the volatiles were removed in vacuo yielding 4-cyclohexenylpyridin-3-amine (99%) as an oil. LCMS (m/z): 175.0 (MH+); LC Rt=1.86 min.

Workup

  1. washeluting with MeOH
  2. customUpon removal of the volatiles in vacuo
  3. dissolutionthe residue was dissolved in EtOAc
  4. washwashed with Na2CO3(sat.), NaCl(sat.)
  5. dry with materialwas dried over MgSO4
  6. filtrationwas filtered
  7. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-6084d809d4344085bf98976ebd7e163f
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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