6-(Benzyloxy)-3-nitropyridin-2-amine → 6-(Benzyloxy)pyridine-2,3-diamine

HRID 1890277Notes

Reaction equation

HRID 1890277 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]([NH2:15])[C:12]([N+:16]([O-])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC(O)=O.[Zn]>[CH2:1]([O:8][C:9]1[N:14]=[C:13]([NH2:15])[C:12]([NH2:16])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 108003796-(Benzyloxy)-3-nitropyridin-2-amine

Product 1

HCID 673118046-(Benzyloxy)pyridine-2,3-diamineYield 97%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 6-(benzyloxy)-3-nitropyridin-2-amine (J. Med. Chem. 1997, 40, 1808) (22.67 g, 92.44 mmol) in AcOH (300 mL) was added zinc dust (24.18 g, 369.7 mmol) in four portions over 10 min while cooling in an ice bath. The mixture was then allowed to warm to room temperature and stirred for 2 h. The mixture was filtered and the solvent was removed under reduced pressure. The product was taken up in EtOAc and washed with saturated NaHCO3 solution and brine. The organics were dried over MgSO4, filtered and concentrated to yield the title compound as a black solid (19.31 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.13 (s, 2H), 5.14 (s, 2H), 5.39 (s, 2H), 5.86 (d, J=7.9 Hz, 1H), 6.77 (d, J=7.9 Hz, 1H), 7.28 (m, 1H), 7.34 (t, J=7.6 Hz, 2H), 7.40 (m, 2H).

Workup

  1. temperaturewhile cooling in an ice bath
  2. filtrationThe mixture was filtered
  3. customthe solvent was removed under reduced pressure
  4. washwashed with saturated NaHCO3 solution and brine
  5. dry with materialThe organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-51573f2995ac48c9894a1ca514798d75
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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