Acetic Acid → HCID 66920605, compound

HRID 1880347Notes

Reaction equation

HRID 1880347 reaction equation
C(O)(=O)C.[CH:5]1([NH:8][NH2:9])[CH2:7][CH2:6]1.Cl.[CH:11](=O)[C:12]([CH3:14])=[O:13]>O>[CH:5]1([NH:8][N:9]=[CH:11][C:12](=[O:13])[CH3:14])[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 880MethylglyoxalHCID 19594968Cyclopropylhydrazine

Product 1

HCID 66920605HCID 66920605, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Acetic acid (1.71 mL, 29.9 mmol) was slowly added to a solution of cyclopropylhydrazine.HCl (2.5 g, 18.1 mmol) in H2O (30 mL), and was then quickly added dropwise to a solution of pyruvaldehyde (40%, 2.36 mL, 14.5 mmol) in H2O (240 mL). This solution was stirred overnight at room temperature. The aqueous layer was salted and extracted with CH2Cl2 (4×). The combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure to give 1.04 g of crude product as a reddish oil. The crude product was purified via flash chromatography (silica gel) eluting with a gradient of ethyl acetate/hexanes (25:75 to 50:50) to afford 637 mg (35%) of 2-oxopropanal cyclopropylhydrazone as a yellow solid.

Workup

  1. extractionextracted with CH2Cl2 (4×)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customto give 1.04 g of crude product as a reddish oil
  5. customThe crude product was purified via flash chromatography (silica gel)
  6. washeluting with a gradient of ethyl acetate/hexanes (25:75 to 50:50)

Sources & evidence

ORD record
ord-0865e2adb545482582995cdf797594a0
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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