Water → HCID 178469092, compound

HRID 872879Notes

Reaction equation

HRID 872879 reaction equation
[CH3:1][O:2][CH2:3][C:4](=O)[CH2:5][C:6](=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8].Cl.Cl.[NH2:16][NH2:17].O.C([O-])(O)=O.[Na+]>C(O)C>[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[NH:17][N:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 17548Hydrazine, dihydrochlorideHCID 516892Sodium BicarbonateHCID 67172400Ethyl 5-methoxy-2,4-dioxopentanoate

Product 1

HCID 178469092HCID 178469092, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 5-methoxy-2,4-dioxopentanoate (2.168 g, 11.52 mmol) was dissolved in ethanol (100 ml) and hydrazine dihydrochloride (4.84 g, 46.1 mmol) was added. The resulting mixture was refluxed for 2 h. 200 ml of water was added and the pH of the mixture was neutralized with NaHCO3. The mixture was extracted with ethyl acetate. The combined organic phases were washed with brine, dried with Na2SO4, filtered and evaporated. The product was used in the next step without further purification. 1H-NMR (400 MHz; DMSO-d6): δ 1.29 (t, 3H), 3.26 (s, 3H), 4.27 (q, 2H), 4.42 (s, 2H), 6.72 (s, 1H), 13.62 (s, 1H).

Workup

  1. temperatureThe resulting mixture was refluxed for 2 h
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-2fe505392c76467d94aa81952655047e
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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