Dichloromethane → HCID 19765069, compound

HRID 248134Notes

Reaction equation

HRID 248134 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1C=O.[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:11])[CH3:10].[OH-].[Na+].Cl[CH2:21]Cl>O>[N:1]1[CH:2]=[CH:3][CH:4]=[C:5]([C:10](=[CH2:21])[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])[CH:6]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7410AcetophenoneHCID 142732-PyridinecarboxaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 19765069HCID 19765069, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 3 pyridinecarboxaldehyde (18.9 mL, 0.20 mol) and acetophenone (23.4 mL, 0.20 mol) in 200 mL water at room temperature with vigorous stirring was added dropwise 5% aqueous sodium hydroxide (200 mL) over a 45-minute period. The reaction mixture was stirred for 12 hours. White solid was formed during the reaction. Dichloromethane (500 mL) was added to dissolve the solid. The organic layer was separated, washed with water (300 mL×3), and dried over anhydrous sodium sulfate. After the drying agent and solvent were removed, the crude product was recrystallized to give the title compound as yellow solid (35.62 g, 85%), mp 113°-114° C.

Workup

  1. stirringThe reaction mixture was stirred for 12 hours
  2. customWhite solid was formed during the reaction
  3. dissolutionto dissolve the solid
  4. customThe organic layer was separated
  5. washwashed with water (300 mL×3)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter the drying agent and solvent were removed
  8. customthe crude product was recrystallized

Sources & evidence

ORD record
ord-eecf4104b8604a1590760825a4349a93
Source dataset
uspto-grants-1993_05
Patent number
US05208343

Reaction notes

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