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

HRID 1074229Notes

Reaction equation

HRID 1074229 reaction equation
[CH2:1]([C:3](=[CH2:6])[CH:4]=O)[CH3:2].[NH2:7][C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]>C(O)(=O)C>[CH2:1]([C:3]1[CH:4]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:7][CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 70203EthylacroleinHCID 71360915Diethyl 2-aminobut-2-enedioate

Product 1

HCID 10857926Diethyl 5-ethylpyridine-2,3-dicarboxylateYield 44.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Glacial acetic acid 100 g and 2-ethyl-2-propenal 30 g (0.357 mol) were placed in a 200 ml four neck distillation flask: with a reflux condenser and heated on an oil bath. When the inside temperature reached 90° C., ethyl β-amino-β-ethoxycarbonylacrylate 60 g (0.321 mol) was added dropwise thereto at 90° to 95° C. over a period of 4 hours. After completion of the dropping, the mixture was reacted at 90° to 95° C. for 3 hours. After completion of the reaction, the reaction mixture was distilled to give 36.2 g of 5-ethyl-2,3-diethoxycarbonylpyridine (bp2 : 151° to 152° C.).

Workup

  1. temperaturewith a reflux condenser and heated on an oil bath
  2. customreached 90° C.
  3. customAfter completion of the dropping, the mixture was reacted at 90° to 95° C. for 3 hours
  4. customAfter completion of the reaction
  5. distillationthe reaction mixture was distilled

Sources & evidence

ORD record
ord-7089702ea5974828916660a281a77435
Source dataset
uspto-grants-1990_11
Patent number
US04973695

Reaction notes

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