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

HRID 2107887Notes

Reaction equation

HRID 2107887 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 gms of ethyl beta-methylaminocinnamate, 9.4 gms of technical grade diketene and 25 mls 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 gms of ethyl 1,6-dimethyl-2-phenyl-4-oxonicotinate. mp (toluene)=244-8.

Workup

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

Sources & evidence

ORD record
ord-13d7d4127eef481a975d0ab059db46d1
Source dataset
uspto-grants-1990_06
Patent number
US04936904

Reaction notes

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