Diethyl Malonate → HCID 58707375, compound

HRID 2390933Notes

Reaction equation

HRID 2390933 reaction equation
[Cl-].[Mg+2].[Cl-].C(N(CC)CC)C.[C:11]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].[Cl:22][C:23]1[N:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26]>C1(C)C=CC=CC=1>[Cl:22][C:23]1[N:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25]([CH:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:11]([O:19][CH2:20][CH3:21])=[O:18])=[O:26]

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 8471TriethylamineHCID 27745412-Chloronicotinoyl chlorideHCID 5360315Magnesium Chloride

Product 1

HCID 58707375HCID 58707375, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
25 °C

Procedure

Magnesium chloride (221 mmol) and triethylamine (752 mmol) were added to a solution of diethyl malonate (375 mmol) in toluene (250 ml) and the reaction mixture was maintained for 1 h at 25° C. A solution of 2-chloronicotinoyl chloride (313 mmol) in toluene (80 mL) was added dropwise over the course of 2 h. The reaction mixture was maintained at rt for 3.5 h and was quenched with cold (0° C.) water (500 mL). The resulting solution was extracted with ethyl acetate (500 mL) and the organic layers combined. The organic layer was washed with brine (3×300 mL), dried (sodium sulfate), and was concentrated to provide diethyl 2-(2-chloronicotinoyl)malonate in 85% yield as a brown oil.

Workup

  1. temperatureThe reaction mixture was maintained at rt for 3.5 h
  2. customwas quenched with cold (0° C.) water (500 mL)
  3. extractionThe resulting solution was extracted with ethyl acetate (500 mL)
  4. washThe organic layer was washed with brine (3×300 mL)
  5. dry with materialdried (sodium sulfate)
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-4fdbb82be2224316bb0cfbaf12d9a8ed
Source dataset
uspto-grants-2012_09
Patent number
US08273891B2

Reaction notes

Loading…