Sodium Hydroxide → Bis(2-pyridyl)methylamine

HRID 1946624

Reaction equation

HRID 1946624 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)=[N:8]O.C([O-])(=O)C.[NH4+].[OH-].[Na+]>C(O)C.[Zn]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[NH2:8]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 73805Di-2-pyridinylmethanone oximeHCID 517165Ammonium Acetate

Product 1

HCID 11106041Bis(2-pyridyl)methylamineYield 61%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

Dipyridin-2-ylmethanone oxime (500 mg, 2.510 mmol) and ammonium acetate were solubilized in ethanol and the mixture was reflux for 3 hours adding portion of zinc at 0 h, 1 h and 2 h. The reaction mixture was cooled down to room temperature and stirred over night. The pH was adjusted to 12 with sodium hydroxide and the mixture was filtered through celite. The mixture was diluted with ethyl acetate and the organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated to afford title compound 405 (282 mg, 61%) as a light yellow oil. MS (m/z): 186.2 (M+H). 1H NMR (CDCl3) δ (ppm): 8.50-8.49 (m, 2H), 7.56 (td, J=7.7, 1.8 Hz, 2H), 7.33 (dt, J=8.0, 0.9 Hz, 2H), 7.08 (ddd, J=7.4, 4.9, 1.2 Hz, 2H), 5.26 (s, 1H), 2.38 (s, 2H).

Workup

  1. temperaturethe mixture was reflux for 3 hours
  2. custom1 h and 2 h
  3. filtrationthe mixture was filtered through celite
  4. additionThe mixture was diluted with ethyl acetate
  5. washthe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-f8ff07573247488285ac5a27ceb1831f
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Linked notes

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