Acetic Acid → HCID 21249899, compound

HRID 1956523Notes

Reaction equation

HRID 1956523 reaction equation
CO[C:3](=[O:18])[C:4]([CH3:17])([CH3:16])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)=O.C(O)(=O)C(O)=O.[CH2:25]([NH:27][NH2:28])[CH3:26].COCCO.C(O)(=O)C>CCCCCC.CCOC(C)=O>[CH2:25]([N:27]1[C:3](=[O:18])[C:4]([CH3:16])([CH3:17])[C:5]([C:7]2[CH:8]=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=2)=[N:28]1)[CH3:26]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 80192-MethoxyethanolHCID 96181Hydrazine, ethyl-, ethanedioate (1:1)HCID 53771006HCID 53771006, compound

Product 1

HCID 21249899HCID 21249899, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 1.00 g (4 mmol) of 2,2-dimethyl-3-(4-nitrophenyl)-3-oxopropionic acid methyl ester (Yang, C.-Y.; Wnek, G. E., Polymer, 1992, 33, 4191-4196), 3.00 g (20 mmol) of ethylhydrazine oxalate, 8 mL of 2-methoxyethanol, and 4 mL of glacial acetic acid was stirred under nitrogen at gentle reflux for 24 hours. The cooled solution was concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The ethyl acetate phase was washed with additional water and then with saturated aqueous sodium chloride solution. The organic solution was dried over magnesium sulfate, filtered, and concentrated in vacuo to give 703 mg (67%) of light yellow crystals, mp 121°-122° C.; homogeneous by TLC in 2:1 hexane-EtOAc. 500 MHz 1H NMR (CDCl3) was consistent with the assigned structure. Mass spectrum (PB-NH3 /CI): m/e=232.1 (M-Et), 265.1 (M+H).

Workup

  1. temperatureat gentle reflux for 24 hours
  2. concentrationThe cooled solution was concentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe ethyl acetate phase was washed with additional water
  5. dry with materialThe organic solution was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give 703 mg (67%) of light yellow crystals, mp 121°-122° C.

Sources & evidence

ORD record
ord-7598c01c21f244bcb48c597526e069b3
Source dataset
uspto-grants-1998_07
Patent number
US05780437

Reaction notes

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