Diketene → HCID 14075281, compound

HRID 986571Notes

Reaction equation

HRID 986571 reaction equation
[CH2:1]([NH:3][C:4]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)=[CH:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[CH2:18]=[C:19]1O[C:21](=[O:22])[CH2:20]1>C(Cl)Cl>[CH2:1]([N:3]1[C:19]([CH3:18])=[CH:20][C:21](=[O:22])[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]1[C:11]1[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=1)[CH3:2]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 70373462HCID 70373462, compound

Product 1

HCID 14075281HCID 14075281, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.64 g of ethyl beta-ethylamino-4-chlorocinnamate, 4.61 g of technical grade diketene and 15 ml of methylene chloride are mixed in a flask fitted with a calcium chloride drying tube. The mixture is maintained at room temperature for 137 hours. The methylene chloride is removed in vacuo and the residue triturated with ether to yield 3.2 g of crude ethyl 1-ethyl-6-methyl-2-(4'-chlorophenyl)-4-oxonicotinate. mp (215°-217° C.).

Workup

  1. customfitted with a calcium chloride drying tube
  2. customThe methylene chloride is removed in vacuo
  3. customthe residue triturated with ether

Sources & evidence

ORD record
ord-61aac8acfd6548ce82bfc05044a5eb61
Source dataset
uspto-grants-1987_12
Patent number
US04714492

Reaction notes

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