Water → HCID 19922432, compound

HRID 1463663Notes

Reaction equation

HRID 1463663 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]#[N:11].Cl.[N:13]1[CH:18]=[CH:17][C:16]([CH2:19]Cl)=[CH:15][CH:14]=1.[OH-].[Na+].O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[N:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:9]([CH2:19][C:16]2[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=2)([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[C:10]#[N:11])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 745704-(Chloromethyl)pyridinium chlorideHCID 81496(2-Methoxyphenyl)acetonitrile

Product 1

HCID 19922432HCID 19922432, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

To a mechanically stirred slurry of (2-methoxyphenyl)acetonitrile (10.0 g, 68 mmol), 4-picolyl chloride hydrochloride (25.0 g, 152 mmol), and 1.2 g benzyltriethylammonium chloride in toluene (200 ml) at room temperature was added 50% NaOH (50 ml) over a period of 15 min. After addition was complete, the reaction mixture was slowly heated to 50° and maintained at that temperature for approx. 3 h. Completion of the reaction was determined by TLC. While still stirring the reaction mixture at 50°, 70 ml of water was added, and stirring was continued for 15 min. The mixture was cooled to room temperature, and the layers were separated. To the toluene layer was added 14.0 g Magneso (an intimate mixture of silica gel and magnesium sulfate), and the solution was stirred at 50° for 30 min. The solution was filtered, and the solvent was removed under reduced pressure. The subsequent oil was purified via column chromatography (silica gel, 10% methanol/methylene chloride) to give α,α-Bis(4-pyridinylmethyl)2-methoxybenzeneacetonitrile as a solid, 16.4 g, 73% yield. NMR (200 MHz, CDCl3) δ 3.26 (d, 2H, J=13 Hz); 3.88 (d, 2H, J=13 Hz); 4.07 (s, 3H); 6.70 (m, 6H); 7.00 (m, 6H); 7.30 (m, 1H); 8.38 (m, 4H). Mass Calcd. for C21H19N3O: 329.1528. Found: 329.1505.

Workup

  1. additionAfter addition
  2. temperaturethe reaction mixture was slowly heated to 50°
  3. temperaturemaintained at that temperature for approx. 3 h
  4. stirringstirring
  5. customthe layers were separated
  6. additionTo the toluene layer was added 14.0 g Magneso (
  7. additionan intimate mixture of silica gel and magnesium sulfate), and the solution
  8. stirringwas stirred at 50° for 30 min
  9. filtrationThe solution was filtered
  10. customthe solvent was removed under reduced pressure
  11. customThe subsequent oil was purified via column chromatography (silica gel, 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-f9032130bc5b4c6eb254d3c219e001e7
Source dataset
uspto-grants-1994_04
Patent number
US05300642

Reaction notes

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