Ethyl Acetoacetate → HCID 178429295, compound

HRID 1878056Notes

Reaction equation

HRID 1878056 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH2:10])=[NH:9])=[N:6][CH:7]=1.C([O:13][C:14](=O)[CH2:15][C:16]([CH3:18])=O)C.C(=O)([O-])[O-].[Na+].[Na+]>O.C(O)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:10]=[C:14]([OH:13])[CH:15]=[C:16]([CH3:18])[N:9]=2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 10340Sodium CarbonateHCID 55289624HCID 55289624, compound

Product 1

HCID 178429295HCID 178429295, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of compound of example 12 (0.4 g, 2.9 mmol) in water (10 mL) and ethanol (5 mL) was added ethylacetoacetate (0.611 g, 4.7 mmol) and sodium carbonate (0.561 g, 5.29 mmol) and mixture was stirred at room temperature for about 25 hours. Ethanol was removed under reduced pressure, and the reaction mixture was diluted with water and extracted with ethyl acetate (3×30 mL). Ethyl acetate layer was dried over anhydrous sodium sulfate and was concentrated to obtain a crude product, which was purified by column chromatography (silica gel, 6% methanol in chloroform as an eluent) to obtain the title compound.

Workup

  1. customEthanol was removed under reduced pressure
  2. additionthe reaction mixture was diluted with water
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. dry with materialEthyl acetate layer was dried over anhydrous sodium sulfate
  5. concentrationwas concentrated
  6. customto obtain a crude product, which
  7. customwas purified by column chromatography (silica gel, 6% methanol in chloroform as an eluent)

Sources & evidence

ORD record
ord-7c2a3b1ca6a54f5ebb57a45ad4cd1bba
Source dataset
uspto-grants-2012_11
Patent number
US08314103B2

Reaction notes

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