2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Ethyl 3-amino-1-(2,4-dimethoxybenzyl)-2-oxo-1,2-dihydropyridine-4-carboxylate

HRID 570730Notes

Reaction equation

HRID 570730 reaction equation
[NH2:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH3:19])[CH2:5][CH2:4][C:3]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C>[NH2:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH3:19])[CH:5]=[CH:4][C:3]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 86685387Ethyl 5-amino-1-(2,4-dimethoxybenzyl)-6-oxo-1,2,3,6-tetrahydropyridine-4-carboxylate

Product 1

HCID 86685389Ethyl 3-amino-1-(2,4-dimethoxybenzyl)-2-oxo-1,2-dihydropyridine-4-carboxylateYield 60.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 5-amino-1-(2,4-dimethoxybenzyl)-6-oxo-1,2,3,6-tetrahydropyridine-4-carboxylate (890 mg) in toluene (20 ml) was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (785 mg) at room temperature, and the mixture was heated under reflux for 30 min, allowed to be cooled to room temperature, and diluted with ethyl acetate. The insoluble material was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (535 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 min
  3. filtrationThe insoluble material was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8451aa8f837c4a58b83a43db5ef4ca5f
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

Loading…