Diketene → HCID 14075281, compound

HRID 2107894Notes

Reaction equation

HRID 2107894 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 gms of ethyl beta-ethylamino-4-chlorocinnamate, 4.61 gms of technical grade diketene and 15 mls 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 gms of crude ethyl 1-ethyl-6-methyl-2-(4'-chlorophenyl)-4-oxonicotinate. mp (215-17).

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-cb7caebbfa874beb929f02e2dcf8453c
Source dataset
uspto-grants-1990_06
Patent number
US04936904

Reaction notes

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