Ethylenediamine → Methyl 1-(2-aminoethyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 2379082Notes

Reaction equation

HRID 2379082 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8](=[O:11])O[CH:10]=1)=[O:4].[NH2:12][CH2:13][CH2:14][NH2:15]>C(O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8](=[O:11])[N:12]([CH2:13][CH2:14][NH2:15])[CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 80113Methyl coumalate

Product 1

HCID 54083902Methyl 1-(2-aminoethyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a 500 ml 3-necked flask fitted with a magnetic stirrer bar, addition funnel, nitrogen inlet, and containing 2-oxo-2H-pyran-5-carboxylic acid methyl ester (coumalic acid methyl ester) (10.0 g, 65.0 mmol) and absolute ethanol 160 ml) was added, over 3-5 minutes at room temperature, a solution consisting of 1,2-diaminoethane (17.4 ml, 260 mmol) and abs. ethanol (50 ml). Stirring was continued for 4 hours at which time the suspension was filtered. Concentration of the flitrate gave 1-(2-aminoethyl)-1,6-dihydro-6-oxo-3-pyridinecarboxylic acid methyl ester which was used without purification.

Workup

  1. customTo a 500 ml 3-necked flask fitted with a magnetic stirrer bar, addition funnel, nitrogen inlet
  2. additionwas added, over 3-5 minutes at room temperature
  3. filtrationthe suspension was filtered

Sources & evidence

ORD record
ord-48794da73a96449893d75c30809f96a3
Source dataset
uspto-grants-1994_11
Patent number
US05360808

Reaction notes

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