Ethyl cyanoacetate → Ethyl 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 2195534

Reaction equation

HRID 2195534 reaction equation
[NH2:1]/[C:2](/[CH3:7])=[CH:3]\[C:4](=O)[CH3:5].[C:8]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])#N.C1C[O:19]CC1>>[CH3:5][C:4]1[CH:3]=[C:2]([CH3:7])[NH:1][C:8](=[O:19])[C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 8028Tetrahydrofuran2×HCID 5355751(3Z)-4-Amino-3-penten-2-one

Product 1

HCID 247443Ethyl 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carboxylateYield 19.9%

Procedure

A solution of (Z)-4-aminopent-3-en-2-one (20.0 g, 0.2 mol) in dry THF (20 mL) is added to a solution of ethyl cyanoacetate (22.6 g, 0.2 mol) and TEA (20.2 g, 0.2 mol) in dry THF (200 mL). The reaction mixture is heated at reflux for 56 hours and then concentrated. The residue is kept standing at RT for 5 hours and the precipitate is filtered and washed with EtOAc to afford the title compound (7.3 g, 19.9% yield). MS (m/z): 196.0 (M+H).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 56 hours
  3. concentrationconcentrated
  4. filtrationthe precipitate is filtered
  5. washwashed with EtOAc

Sources & evidence

ORD record
ord-bd55881dac5046d0ab7131fcbf7111b7
Source dataset
uspto-grants-2012_12
Patent number
USRE043878E1

Linked notes

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