Sodium Hydroxide → HCID 5205748, compound

HRID 2416369Notes

Reaction equation

HRID 2416369 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1)C#N.[OH-].[Na+]>OS(O)(=O)=O.O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 12621791HCID 12621791, compound

Product 1

HCID 5205748HCID 5205748, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

Bis(2-quinolinyl)acetonitrile (14.3 g, 48.4 mmol) was dissolved in 70% H2SO4 in H2O (85 mL), and the resulting solution was heated at reflux for 1.5 h. The reaction mixture was poured into a 2-L beaker full of ice and was neutralized very carefully with a NaOH solution. The aqueous solution was extracted with a mixture of ether and THF, and the organic layer was isolated and dried over MgSO4. The volatile components were removed, and the resulting solid was washed with a solution of heptane and ether to afford 11.7 g (89.5%) of bis(2-quinolinyl)methane as a reddish powder. Results of 1H NMR spectroscopy and electrospray mass spectroscopy are consistent with the product. 1H NMR (300 MHz, CDCl3): δ 4.74 (s, 2H), 7.42 (d, J=8.5 Hz, 2H), m, 2H), 7.51 (m, 2H), 7.72 (m, 2H), 7.77 (d, J=8.2 Hz, 2H), 8.04 (d, J=8.5 Hz, 2H), 8.11 (d, J=8.5 Hz, 2H).

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux for 1.5 h
  3. additionThe reaction mixture was poured into a 2-L beaker full of ice
  4. extractionThe aqueous solution was extracted with a mixture of ether and THF
  5. customthe organic layer was isolated
  6. dry with materialdried over MgSO4
  7. customThe volatile components were removed
  8. washthe resulting solid was washed with a solution of heptane and ether

Sources & evidence

ORD record
ord-4adc390641e54ff1a24c7696214480c5
Source dataset
uspto-grants-2004_11
Patent number
US06824893B2

Reaction notes

Loading…