2,2',4,4'-Tetrahydroxybenzophenone → HCID 136358437, compound

HRID 1294892Notes

Reaction equation

HRID 1294892 reaction equation
O[C:2]1[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[OH:13])=O.C([O-])(=O)C.[Na+].Cl.Cl.[CH2:26]([NH:33][NH2:34])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O>[CH2:26]([N:33]1[C:2]2[C:3](=[CH:14][CH:15]=[C:16]([OH:18])[CH:17]=2)[C:4]([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=2[OH:13])=[N:34]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 85712,2',4,4'-TetrahydroxybenzophenoneHCID 146540Benzylhydrazine dihydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 136358437HCID 136358437, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2,2′,4,4′-tetrahydroxybenzophenone (0.123 g, 0.5 mmol), sodium acetate (0.164 g, 2.0 mmol) and benzylhydrazine dihydrochloride (0.39 g, 2.0 mmol) in 2 mL H2O was heated at 90° C. overnight. The cooled reaction mixture was partitioned with EtOAc and 1 N HCl. The organic layer was dried (Na2SO4) and concentrated in vacuo to give the crude product. The residue was purified by HPLC chromatography using a silica gel column 150×12 mm (Biotage) at 10 mL/min with methyl-t-butyl ether/hexane (1:3, v/v) to give 0.062 g of product as an amber solid.

Workup

  1. customThe cooled reaction mixture
  2. customwas partitioned with EtOAc and 1 N HCl
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. customThe residue was purified by HPLC chromatography

Sources & evidence

ORD record
ord-be64533d4e9b458f8d3092209086e728
Source dataset
uspto-grants-2007_07
Patent number
US07241791B2

Reaction notes

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