Methylhydrazine → HCID 56946410, compound

HRID 221812Notes

Reaction equation

HRID 221812 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=O)[CH3:11])=[CH:5][CH:4]=1.O.[C:14]([OH:18])(=O)[CH:15]=O.[CH3:19][NH:20][NH2:21]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([CH3:11])=[N:21][N:20]([CH3:19])[C:14](=[O:18])[CH:15]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 6061MethylhydrazineHCID 312311-(p-Methoxyphenyl)-2-propanoneHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 56946410HCID 56946410, compoundYield 18.2%

Conditions

Temperature
135 °C

Procedure

A mixture of 1-(4-methoxyphenyl)propan-2-one (16.4 g, 100 mmol) and glyoxalic acid hydrate (9.20 g, 100 mmol) were heated to 135° C. overnight, then the water was distilled off at 120° C. for 2 h. The residue was taken up in 40 mL of ethanol with stirring as methylhydrazine (10.5 mL, 200 mmol) was added dropwise. The reaction was heated to 85° C. overnight. The solvent was evaporated and the residue was dissolved in 200 mL of methylene chloride and washed with 5% NaHCO3 solution (2×20 mL), saturated NaCl solution, then dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (2% MeOH in CH2Cl2) to give 5-(4-methoxyphenyl)-2,6-dimethyl-2H-pyridazin-3-one (4.2 g) MS m/z 231 (M+H).

Workup

  1. distillationthe water was distilled off at 120° C. for 2 h
  2. additionwas added dropwise
  3. temperatureThe reaction was heated to 85° C. overnight
  4. customThe solvent was evaporated
  5. dissolutionthe residue was dissolved in 200 mL of methylene chloride
  6. washwashed with 5% NaHCO3 solution (2×20 mL), saturated NaCl solution
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography (2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-3ffe477df50d4b179b8f26fc6d569fb6
Source dataset
uspto-grants-2012_06
Patent number
US08207168B2

Reaction notes

Loading…