Potassium Carbonate → Benzyl ethyl 2-(6-nitro-3-pyridinyl)malonate

HRID 858510Notes

Reaction equation

HRID 858510 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[C:11]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C([O-])([O-])=O.[K+].[K+]>O1CCCC1.CN(C)C=O.O>[N+:8]([C:5]1[N:6]=[CH:7][C:2]([CH:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:11]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 562228Benzyl ethyl malonateHCID 8176205-Bromo-2-nitropyridine

Product 1

HCID 21875897Benzyl ethyl 2-(6-nitro-3-pyridinyl)malonateYield 35.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5-bromo-2-nitropyridine (8.66 g, 42.7 mmol) and benzyl ethyl malonate (9.50 g, 42.7 mmol) in tetrahydrofuran (160 ml) and dimethylformamide (40 ml) was added K2CO3 (5.90 g, 42.7 mmol) and stirred under reflux temperature for 20 h. The mixture was diluted with water (11) and extracted with ethyl acetate (3×200 ml). The organic layer was washed with brine, dried (MgSO4) and concentrated to give 5.26 g of title compound as orange oil.

Workup

  1. temperatureunder reflux temperature for 20 h
  2. extractionextracted with ethyl acetate (3×200 ml)
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cbf23588bdb047f199ce21df5c106279
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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