Dichloromethane → Ethyl 1,6-dimethyl-2-phenyl-4-oxonicotinate

HRID 1089045Notes

Reaction equation

HRID 1089045 reaction equation
[CH3:1][NH:2][C:3]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[CH:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH2:16]=[C:17]1O[C:19](=[O:20])[CH2:18]1.C(Cl)Cl>CCOCC>[CH3:1][N:2]1[C:17]([CH3:16])=[CH:18][C:19](=[O:20])[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:3]1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 12661DiketeneHCID 58005139Ethyl 3-(methylamino)-3-phenylacrylate

Product 1

HCID 14075276Ethyl 1,6-dimethyl-2-phenyl-4-oxonicotinate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

10.25 g of ethyl beta-methylaminocinnamate, 9.4 g of technical grade diketene and 25 ml dry methylene chloride are mixed in a flask fitted with a calcium chloride drying tube. The reaction mixture is stored at room temperature for 117 hours. Approximately 75 ml of dry ether is added and the resulting crystalline solid is filtered to yield 8.5 g of ethyl 1,6-dimethyl-2-phenyl-4-oxonicotinate. mp (toluene)=244°-248° C.

Workup

  1. customfitted with a calcium chloride drying tube
  2. filtrationthe resulting crystalline solid is filtered

Sources & evidence

ORD record
ord-4484774cd78c4cee876859c9c3dda936
Source dataset
uspto-grants-1990_10
Patent number
US04964896

Reaction notes

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