Diethyl Malonate → HCID 70197351, compound

HRID 2269738Notes

Reaction equation

HRID 2269738 reaction equation
C(=O)([O-])O.[K+].C(OC(=O)C)(=O)C.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([N+:22]([O-:24])=[O:23])=[C:18]([CH:21]=1)[CH:19]=O.[C:25]([O:33][CH2:34][CH3:35])(=[O:32])[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>O>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([N+:22]([O-:24])=[O:23])=[C:18]([CH:19]=[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:25]([O:33][CH2:34][CH3:35])=[O:32])[CH:21]=1

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 7918Acetic AnhydrideHCID 811235-Chloro-2-nitrobenzaldehydeHCID 516893Potassium Bicarbonate

Product 1

HCID 70197351HCID 70197351, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

Potassium hydrogen carbonate (8.12 g) was added to an acetic acid anhydride (18 ml) solution of 5-chloro-2-nitrobenzaldehyde (9.99 g) and diethyl malonate (8.64 g), which was stirred at 110° C. for 2 hours. The reaction mixture was added to iced-water and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried and concentrated. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/10) to obtain the entitled compound (15.10 g). 1H-NMR δ: 1.10(3H, t), 1.36(3H, t), 4.15(2H, q), 4.44(2H, q), 7.42(1H, d), 7.52(1H, dd), 8.11(1H, s), 8.18(1H, d).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, then dried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/10)

Sources & evidence

ORD record
ord-e115e0c1cda9438e806031d0d4478649
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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