Pyridine → HCID 18937850, compound

HRID 1489499Notes

Reaction equation

HRID 1489499 reaction equation
N1C=C[CH:4]=[CH:3][CH:2]=1.[NH2:7]/[C:8](=[C:14](\Cl)/[C:15]([O:17][CH2:18][CH3:19])=[O:16])/[C:9]([O:11][CH2:12][CH3:13])=[O:10].[CH3:21][O:22]C(C=C)=O>C(O)(=O)C>[CH3:21][O:22][C:3]1[CH:4]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:7][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7294Methyl AcrylateHCID 14745921HCID 14745921, compound

Product 1

HCID 18937850HCID 18937850, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

83 g (1.05 mol) of pyridine were added to 221.5 (1.0 mol) of diethyl 2-amino-3-chloromaleate in 250 ml of glacial acetic acid at 80° C. while stirring. 90 g (1.05 mol) of methoxyacrolein were then added at 120° C. in the course of 30 minutes, gentle refluxing being established without heating. The reaction mixture was stirred for 3 hours at 120° C. and then evaporated down under reduced pressure, water was added to the residue and the mixture was extracted with methylene chloride. After filtration of active carbon, drying, filtration over neutral alumina with suction and evaporating down under reduced pressure, 190 g (75% of theory) of the title compound were obtained as a pale yellow syrup.

Workup

  1. temperaturegentle refluxing
  2. temperaturewithout heating
  3. stirringThe reaction mixture was stirred for 3 hours at 120° C.
  4. customevaporated down under reduced pressure, water
  5. additionwas added to the residue
  6. extractionthe mixture was extracted with methylene chloride
  7. filtrationAfter filtration of active carbon
  8. customdrying
  9. filtrationfiltration over neutral alumina with suction
  10. customevaporating down under reduced pressure, 190 g (75% of theory) of the title compound
  11. customwere obtained as a pale yellow syrup

Sources & evidence

ORD record
ord-3ecb4cb526644cec92c37b3f0aa4b3f8
Source dataset
uspto-grants-1997_10
Patent number
US05679622

Reaction notes

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