Acetic Acid → HCID 178434632, compound

HRID 1488176Notes

Reaction equation

HRID 1488176 reaction equation
[CH:1]1([CH:4]([C:7](=O)[CH3:8])[C:5]#[N:6])[CH2:3][CH2:2]1.CC(O)=O.O.[NH2:15][NH2:16].C([O-])(O)=O.[Na+]>C(O)C.O>[CH:1]1([C:4]2[C:7]([CH3:8])=[N:15][NH:16][C:5]=2[NH2:6])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 23631356HCID 23631356, compound2×

Product 1

HCID 178434632HCID 178434632, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Into a 250-mL round-bottom flask, was placed a solution of 2-cyclopropyl-3-oxobutanenitrile (compound 266.1, 4.0 g, 32.5 mmol) in ethanol (18 mL). AcOH (3 mL) and hydrazine hydrate (3.15 mL, 65 mmol) were added and the reaction was stirred overnight at 80° C. The reaction was cooled, then the pH was carefully adjusted to 9 with NaHCO3 (aq. sat.). The mixture was diluted with water, then extracted with ethyl acetate (6×60 mL) and the combined organic extracts were washed with brine (80 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to obtain the title compound as a brown oil (4.17 g, crude), which was used in the next step without purification.

Workup

  1. customInto a 250-mL round-bottom flask, was placed
  2. temperatureThe reaction was cooled
  3. extractionextracted with ethyl acetate (6×60 mL)
  4. washthe combined organic extracts were washed with brine (80 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-53127aab08d74713a019987d41d62d3d
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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