Methacrolein → Diethyl 5-methylpyridine-2,3-dicarboxylate

HRID 1074231Notes

Reaction equation

HRID 1074231 reaction equation
[NH2:1][C:2]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:14][C:15](=[CH2:18])[CH:16]=O>C(O)(=O)C>[CH3:18][C:15]1[CH:14]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:1][CH:16]=1

Participants

4

Reactant 2

HCID 6562MethacroleinHCID 71360915Diethyl 2-aminobut-2-enedioate

Product 1

HCID 11806659Diethyl 5-methylpyridine-2,3-dicarboxylateYield 28.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl β-amino-β-ethoxycarbonylacrylate 18.7 g (0.1 mol), 2-methyl-2-propenal 7.5 g (0.107 mol), and glacial acetic acid 50 g were placed in a 100 ml four neck distillation flask with a reflux condenser and the temperature of the mixture was raised to 80° C. on an oil bath over a period of 1 hour. Then, the mixture was reacted at 80° to 85° C. for 5 hours. After completion of the reaction, the reaction mixture was distilled to give 6.8 g of 5-methyl-2,3-diethoxycarbonylpyridine (bp3.5 : 160° to 161° C.).

Workup

  1. customThen, the mixture was reacted at 80° to 85° C. for 5 hours
  2. customAfter completion of the reaction
  3. distillationthe reaction mixture was distilled

Sources & evidence

ORD record
ord-20baba0da1f74bcf956c4e48ee72d1ae
Source dataset
uspto-grants-1990_11
Patent number
US04973695

Reaction notes

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