Diethyl (2,6-dichloronicotinoyl)-malonate → Ethyl 3-(2,6-dichloropyridin-3-YL)-3-oxopropanoate

HRID 2209984Notes

Reaction equation

HRID 2209984 reaction equation
[Cl:1][C:2]1[N:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[C:4]([CH:6](C(OCC)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:1][C:2]1[N:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]

Participants

4

Reactant 1

HCID 22077288Diethyl (2,6-dichloronicotinoyl)-malonate

Product 1

HCID 44140080Ethyl 3-(2,6-dichloropyridin-3-YL)-3-oxopropanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6101p-Toluenesulfonic acidSolvent

Procedure

The crude diethyl (2,6-dichloronicotinoyl)-malonate is refluxed for 2 hours in 45 ml of water and 90 mg of p-toluenesulphonic acid. The mixture is extracted using methylene chloride, and the methylene chloride phase is washed with water, dried over sodium sulphate and concentrated in vacuo. The crude product is purified on silica gel (eluent dichloromethane).

Workup

  1. extractionThe mixture is extracted
  2. washthe methylene chloride phase is washed with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified on silica gel (eluent dichloromethane)

Sources & evidence

ORD record
ord-96f345fc899f476b8d89da6f2a51e32d
Source dataset
uspto-grants-1995_10
Patent number
US05457104

Reaction notes

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