Methylhydrazine → HCID 59260113, compound

HRID 642999Notes

Reaction equation

HRID 642999 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][CH:5]=1)=O.O.[C:12]([OH:16])(=O)[CH:13]=O.[OH-].[NH4+].[CH3:19][NH:20][NH2:21]>C(O)(=O)C.C(OCC)(=O)C>[I:10][C:7]1[CH:8]=[CH:9][C:4]([C:2]2[CH:1]=[CH:13][C:12](=[O:16])[N:20]([CH3:19])[N:21]=2)=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 6061MethylhydrazineHCID 14923Ammonium HydroxideHCID 728691-(4-Iodophenyl)ethan-1-oneHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 59260113HCID 59260113, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 4-iodoacetophenone (1.00 g, 4.06 mmol) and glyoxalic acid monohydrate (0.45 g, 4.9 mmol) in 20 mL acetic acid was refluxed for 18 hrs before concentrated in vacuo. The dry residue was then stirred in 15 mL water to form a slurry material. To it was added carefully with ammonium hydroxide (30%) until pH 9 as indicated by pH paper. The pH was critical for this reaction. Methylhydrazine (0.43 mL) was added, and the reaction was sent to 100° C. bath for 3 hrs before the mixture was diluted with ethyl acetate. The organic phase was washed with brine, dried, concentrated in vacuo, and purified by flash column using 5% methanol in DCM isocratically to yield 6-(4-iodophenyl)-2-methylpyridazin-3(2H)-one (680 mg, 54%). MS found for C11H91N2O (M+H)+ 313.0.

Workup

  1. temperaturewas refluxed for 18 hrs
  2. concentrationbefore concentrated in vacuo
  3. customto form a slurry material
  4. customThe pH was critical for this reaction
  5. customwas sent to 100° C.
  6. customfor 3 hrs
  7. washThe organic phase was washed with brine
  8. customdried
  9. concentrationconcentrated in vacuo
  10. custompurified by flash column

Sources & evidence

ORD record
ord-02c6a58b45fe4cc4a98cedc6fb4f0447
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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