Potassium Hydroxide → 3,3'-Methylenedipyridine

HRID 1360121Notes

Reaction equation

HRID 1360121 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=O)[CH:2]=1.[OH-].[K+].O.NN>C(O)CO.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:2]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 298471Di-3-pyridinylmethanone

Product 1

HCID 147626403,3'-Methylenedipyridine

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Procedure

Dipyridin-3-ylmethanone (1-1, 2.630 g, 14.28 mmol) was suspended in ethylene glycol (28 mL). KOH (1.682 g, 29.98 mmol) was added and the reaction was stirred at RT for 1 hr until most of the solids were dissolved. Hydrazine monohydrate (1.596 mL, 32.84 mmol) was added and the mixture was heated to 185° C. After 1 hr 45 min, the reaction was cooled to RT, diluted with H2O (150 mL), and extracted with CH2Cl2 (4×100 mL). The combined organics were washed with water, washed with brine (2×), dried over Na2SO4, filtered, and concentrated in vacuo to afford 3-(pyridin-3-ylmethyl)pyridine as a light yellow solid. 1H NMR (CDCl3) δ 8.52-8.49 (m, 4H), 7.47-7.45 (m, 2H), 7.25-7.22 (m, 2H), 3.99 (s, 2H). [M+H]+=171.2.

Workup

  1. dissolutionwere dissolved
  2. temperaturethe mixture was heated to 185° C
  3. waitAfter 1 hr 45 min
  4. temperaturethe reaction was cooled to RT
  5. extractionextracted with CH2Cl2 (4×100 mL)
  6. washThe combined organics were washed with water
  7. washwashed with brine (2×)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-27e66d52a9c14adfb0c9ad8dca594910
Source dataset
uspto-grants-2011_02
Patent number
US07879839B2

Reaction notes

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