Dimethylformamide → 4-{2-[Methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

HRID 1058090Notes

Reaction equation

HRID 1058090 reaction equation
CN(C)C=O.[CH3:6][N:7]([CH2:14][CH2:15][OH:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.F[C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1.CC(C)([O-])C.[K+]>O>[CH3:6][N:7]([CH2:14][CH2:15][O:16][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 680234-FluorobenzaldehydeHCID 7374202-(N-Methyl-N-(2-pyridyl)amino)ethanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 104225464-{2-[Methyl(pyridin-2-yl)amino]ethoxy}benzaldehydeYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 2l three necked, round bottom flask, 500 ml dimethylformamide is added, followed by addition of 100 g of 2-(N-methyl-N-(2-pyridyl)amino)ethanol (II) and 100 g of 4-fluorobenzaldehyde (III) was added to the reaction mixture and it was stirred for 10 minutes at room temperature and 80 g of potassium tertiary butoxide was added to the reaction mixture. The reaction was monitored by TLC. After completion of the reaction, the reaction mixture was cooled to 5-10° C. and under the cold conditions, 1.5 l of water was added and stirred for 15 min. The mixture was extracted with 4×500 ml of ethyl acetate. The combined organic layer was washed with 3×1 l water. The organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to give 148 g (88%) of 4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy)benzaldehyde (IV).

Workup

  1. additionwas added to the reaction mixture and it
  2. customAfter completion of the reaction
  3. additionwas added
  4. stirringstirred for 15 min
  5. extractionThe mixture was extracted with 4×500 ml of ethyl acetate
  6. washThe combined organic layer was washed with 3×1 l water
  7. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b8953ad80de546a5b001355f2dbfc465
Source dataset
uspto-grants-2003_02
Patent number
US06515132B2

Reaction notes

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