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

HRID 986565Notes

Reaction equation

HRID 986565 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-4c7d3e8b011a413ea63b1f62ce7b3992
Source dataset
uspto-grants-1987_12
Patent number
US04714492

Reaction notes

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