Sulfuric Acid → HCID 136365341, compound

HRID 2422996Notes

Reaction equation

HRID 2422996 reaction equation
[NH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[NH2:2].S(=O)(=O)(O)O.[CH3:14][C:15]([C:17]1[CH:18]=[CH:19][C:20]([OH:24])=[CH:21][C:22]=1[OH:23])=O>CO>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[NH:1][N:2]=[C:15]([C:17]1[CH:18]=[CH:19][C:20]([OH:24])=[CH:21][C:22]=1[OH:23])[CH3:14]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 69902',4'-DihydroxyacetophenoneHCID 786452-Hydrazinopyridine

Product 1

HCID 136365341HCID 136365341, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A total of 33.8 g (0.309 mol) of 2-hydrazinopyridine and 2 L of methanol were charged into a four-neck flask with a capacity of 3 L equipped with a reflux condenser, a thermometer, and a stirrer, and 1 mL of concentrated sulfuric acid was then dropwise added at room temperature under stirring. Then, 44.0 g (0.289 mol) of 2,4-dihydroxyacetophenone was charged and a reaction was conducted for 8 h at 40° C. under stirring. The precipitated crystals were taken out by filtration, washed with methanol and water and dried at 60° C. to obtain 33.0 g of 4-{1-[(2-pyridine-2-yl)hydrazono]ethyl}benzene-1,3-diol in the form of light-yellow crystals. The yield was 50%. GC/MS, 1H-NMR, and IR measurements were performed with respect to the obtained crystals. The results are shown below.

Workup

  1. customequipped with a reflux condenser
  2. stirringunder stirring
  3. filtrationThe precipitated crystals were taken out by filtration
  4. washwashed with methanol and water
  5. customdried at 60° C.

Sources & evidence

ORD record
ord-9be14210f6da4853a9081da0d98da974
Source dataset
uspto-grants-2011_06
Patent number
US07960501B2

Reaction notes

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