Acetic Acid → HCID 86753394, compound

HRID 1456405Notes

Reaction equation

HRID 1456405 reaction equation
OCCN=[C:5]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[NH2:19])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12].[CH2:20]([O:22][CH:23]([O:26][CH2:27][CH3:28])[CH2:24][NH2:25])[CH3:21].C(O)(=O)C>C(O)C>[CH2:20]([O:22][CH:23]([O:26][CH2:27][CH3:28])[C:24](=[C:5]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[NH2:19])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])[NH2:25])[CH3:21]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 695242,2-DiethoxyethylamineHCID 22105989HCID 22105989, compound

Product 1

HCID 86753394HCID 86753394, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-hydroxy-N-[α-(3-amino-4-pyridyl)-2-chlorobenzylidene]-ethylamine (6.28 g, 22 mmol), aminoacetaldehyde diethyl acetal (10 g, 75.1 mmol) and acetic acid (3 ml) in ethanol (150 ml) was refluxed for 30 hours. The mixture was concentrated under reduced pressure, and to the residue was added water, and the mixture was extracted with ethyl acetate. The extract was washed with water, washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel; methanol: chloroform=1:9) to give the title compound (4.27 g, 11.9 mmol) as a pale yellow solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionto the residue was added water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. washwashed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography (silica gel; methanol: chloroform=1:9)

Sources & evidence

ORD record
ord-308cbb4c25aa42138e0e467bff3d97d4
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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