Potassium Carbonate → Diethyl 2-((1-(4-methoxybenzyl)-2-oxo-1,2-dihydropyridin-3-ylamino)methylene)malonate

HRID 2092333Notes

Reaction equation

HRID 2092333 reaction equation
[O:1]=[C:2]1[C:7]([NH:8][CH:9]=[C:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=[CH:4][NH:3]1.C(=O)([O-])[O-].[K+].[K+].[CH3:27][O:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Cl)=[CH:31][CH:30]=1>CN(C=O)C.O>[CH3:27][O:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][N:3]2[CH:4]=[CH:5][CH:6]=[C:7]([NH:8][CH:9]=[C:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:2]2=[O:1])=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 12868403Diethyl 2-((2-oxo-1,2-dihydropyridin-3-ylamino)methylene)malonate

Product 1

HCID 67340511Diethyl 2-((1-(4-methoxybenzyl)-2-oxo-1,2-dihydropyridin-3-ylamino)methylene)malonateYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Diethyl 2-((2-oxo-1,2-dihydropyridin-3-ylamino)methylene)malonate (7.50 g, 26.8 mmol) was dissolved in DMF (30 ml) and treated with potassium carbonate (7.40 g, 53.5 mmol) and 4-methoxybenzyl chloride (5.45 ml, 40.1 mmol). The mixture was stirred at ambient temperature overnight. The reaction was diluted with water (150 ml) and the solid that crashed out was collected by suction filtration. The solid was washed with water and dried to give diethyl 2-((1-(4-methoxybenzyl)-2-oxo-1,2-dihydropyridin-3-ylamino)methylene)malonate (9.00 g, 84.0% yield) as a light green solid. MS(M+H)+ 401.

Workup

  1. filtrationthe solid that crashed out was collected by suction filtration
  2. washThe solid was washed with water
  3. customdried

Sources & evidence

ORD record
ord-881dc6433660461989dbaf2a8fb1d32b
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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