HCID 86753394, compound → HCID 22106198, compound

HRID 1456406Notes

Reaction equation

HRID 1456406 reaction equation
C(O[CH:4](OCC)[C:5](=[C:7]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[NH2:21])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14])[NH2:6])C>Cl.C(O)C>[NH2:6][C:5]1[CH:4]=[N:21][C:16]2[C:15]([C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14])=[CH:20][CH:19]=[N:18][CH:17]=2

Participants

4

Reactant 1

HCID 86753394HCID 86753394, compound

Product 1

HCID 22106198HCID 22106198, compoundYield 34.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

2,2-Diethoxy-N-[α-(3-amino-4-pyridyl)-2-chlorobenzylidene]ethylamine (4.00 g, 11.17 mmol) was dissolved in 10% hydrogen chloride in ethanol (60 ml), and the mixture was refluxed for 5 hours. The mixture was concentrated under reduced pressure, and to the residue was added a saturated aqueous sodium hydrogen carbonate solution, 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=1:19) to give the title compound (0.99 g, 3.87 mmol) as a colorless solid.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionto the residue was added a saturated aqueous sodium hydrogen carbonate solution
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. washwashed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography (silica gel; methanol:chloroform=1:19)

Sources & evidence

ORD record
ord-3e7d9fdf9261482d929ca4a68851506b
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

Loading…