Ethylacrolein → Diethyl 5-ethylpyridine-2,3-dicarboxylate

HRID 1074232Notes

Reaction equation

HRID 1074232 reaction equation
C(O)(=O)/C=C\C(O)=O.[CH2:9]([C:11](=[CH2:14])[CH:12]=O)[CH3:10].[NH2:15][C:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(O)(C)C>[CH2:9]([C:11]1[CH:12]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:15][CH:14]=1)[CH3:10]

Participants

5

Reactant 3

HCID 70203EthylacroleinHCID 444266Maleic AcidHCID 71360915Diethyl 2-aminobut-2-enedioate

Product 1

HCID 10857926Diethyl 5-ethylpyridine-2,3-dicarboxylateYield 37.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

Isopropyl alcohol 150 ml and maleic acid 30.7 g (0 264 mol) were placed in 200 ml four-neck flask equipped with a reflux condenser. After heating the content to 70° C., a mixture of 22.2 g (0.264 mol) of 2-ethyl-2-propenal and 32.9 g (0.176 mol) of ethyl β-amino-β-ethoxycarbonylacrylate were added dropwise thereto with air-bubbling and refluxed for 10 hours. After removal of isopropyl alcohol, 100 ml of water was added thereto and the reaction mixture was neutralized with sodium carbonate. Oil layer was separated and concentrated under reduced pressure to obtain 16.5 g of 5-ethyl-2,3-diethoxycarbonylpyridine.

Workup

  1. customequipped with a reflux condenser
  2. additionwere added dropwise
  3. customwith air-bubbling
  4. temperaturerefluxed for 10 hours
  5. customAfter removal of isopropyl alcohol, 100 ml of water
  6. additionwas added
  7. customOil layer was separated
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-45633b688afc4090a2e817cf33b4ad76
Source dataset
uspto-grants-1990_11
Patent number
US04973695

Reaction notes

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