Diethyl Malonate → HCID 86683907, compound

HRID 2405008Notes

Reaction equation

HRID 2405008 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].Br[C:13]1[C:14](=[O:30])[N:15]([C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=2[O:28][CH3:29])[CH:16]=[CH:17][CH:18]=1>O1CCOCC1>[CH3:29][O:28][C:20]1[CH:21]=[C:22]([N+:25]([O-:27])=[O:26])[CH:23]=[CH:24][C:19]=1[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])[C:14]1=[O:30]

Participants

4

Reactant 2

HCID 7761Diethyl MalonateHCID 594101453-Bromo-1-(2-methoxy-4-nitrophenyl)pyridin-2(1H)-one

Product 1

HCID 86683907HCID 86683907, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

39.3 g of sodium tert-butylate (0.41 mol) were introduced as initial charge in 300 ml of dioxane, and 65.5 g of diethyl malonate (0.41 mol) were added dropwise over the course of 15 min such that the temperature does not exceed 30° C. After 1 h, 2.70 g (8.8 mmol) of bis(2-pyridinecarboxylato)copper(II) complex and 38.0 g (0.12 mol) of 3-bromo-1-(2-methoxy-4-nitrophenyl)pyridin-2(1H)-one were added and the reaction mixture was heated at reflux for 8 h. After cooling to RT, the mixture was further stirred overnight. The reaction mixture was filtered off from the solid with suction, the residue was after-washed with dioxane and the combined organic fractions were evaporated to ca. 300 g on a rotary evaporator. The crude solution was used in the next stage without further purification.

Workup

  1. customdoes not exceed 30° C
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 8 h
  4. waitthe mixture was further stirred overnight
  5. filtrationThe reaction mixture was filtered off from the solid with suction
  6. washthe residue was after-washed with dioxane
  7. customthe combined organic fractions were evaporated to ca. 300 g on a rotary evaporator
  8. customThe crude solution was used in the next stage without further purification

Sources & evidence

ORD record
ord-9a0f2215438f439289c528eadb07a08d
Source dataset
uspto-grants-2014_08
Patent number
US08802860B2

Reaction notes

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