2-(Ethylamino)ethanol → 4-(Ethyl(2-hydroxyethyl)amino)benzaldehyde

HRID 1416336Notes

Reaction equation

HRID 1416336 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10]([NH:12][CH2:13][CH2:14][OH:15])[CH3:11].C(=O)([O-])[O-].[K+].[K+].CCCCCCCC(C([NH3+])(C(CCCCCCC)=O)C(CCCCCCC)=O)=O.[Cl-].[Cl-].C([N+](C(=O)CCCCCCC)(C(=O)CCCCCCC)C)(=O)CCCCCCC>CS(C)=O>[CH2:10]([N:12]([C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH2:13][CH2:14][OH:15])[CH3:11]

Participants

7

Reactant 5

HCID 80722-(Ethylamino)ethanolHCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 14567419HCID 14567419, compoundHCID 77620884Tricaprylylmethyl ammonium chloride

Product 1

HCID 6398574-(Ethyl(2-hydroxyethyl)amino)benzaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

A one liter three-neck flask, fitted with mechanical stirrer, thermometer, and condenser, was charged with 25 g (0.2 mol) of 4-fluorobenzaldehyde), 54 g (0.6 mol) of 2-(ethylamino)ethanol, 41.5 g (0.3 mol) of anhydrous potassium carbonate, and 0.5 ml ALIQUAT-336™ (tricaprylyl methylammonium chloride) (Henkel Corp.) in 250 ml dimethylsulfoxide ("DMSO"). The reaction mixture was heated at 95° C. for 72 hours, cooled to room temperature, and then poured into an ice water mixture. The water layer was extracted with dichloromethane, and the combined organics were washed twice with cold water. After solvent evaporation, the red-colored oil was dissolved in 200 ml of ether and poured into 800 ml of 1N aqueous HCl. After stirring for 10 minutes, the water layer was separated and neutralized using aqueous sodium carbonate. 200 ml dichloromethane were added, and the organic layer was separated and dried with anhydrous sodium sulfate. Removal of the solvent afforded 4-(N-ethyl-N-hydroxyethylamino)benzaldehyde as a pale yellow oil. Yield 25 g (65%); 1H-NMR (CDCl3) δ1.18 (t, 3H), 2.30 (s, 1H), 3.62 (m, 2H), 3.66 (t, 2H), 3.90 (t, 2H), 6.70 (d, 2H), 7.68 (d, 2H), 9.62 (s, 1H) ppm.

Workup

  1. customA one liter three-neck flask, fitted with mechanical stirrer
  2. temperaturecooled to room temperature
  3. extractionThe water layer was extracted with dichloromethane
  4. washthe combined organics were washed twice with cold water
  5. customAfter solvent evaporation
  6. dissolutionthe red-colored oil was dissolved in 200 ml of ether
  7. additionpoured into 800 ml of 1N aqueous HCl
  8. customthe water layer was separated
  9. addition200 ml dichloromethane were added
  10. customthe organic layer was separated
  11. dry with materialdried with anhydrous sodium sulfate
  12. customRemoval of the solvent

Sources & evidence

ORD record
ord-c0e9424ec0db45338b2d943b77502e1a
Source dataset
uspto-grants-1999_06
Patent number
US05912257

Reaction notes

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