2,2',4,4'-Tetrahydroxybenzophenone → HCID 135516837, compound

HRID 1294890Notes

Reaction equation

HRID 1294890 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.[Cl-].[NH4+].Cl.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH:29][NH2:30]>O>[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]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:30]1

Participants

5

Reactant 3

HCID 85712,2',4,4'-TetrahydroxybenzophenoneHCID 25517Ammonium ChlorideHCID 4432872-Chlorophenylhydrazine hydrochloride

Product 1

HCID 135516837HCID 135516837, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,2′,4,4′-tetrahydroxybenzophenone (0.246 g, 1.0 mmol), ammonium chloride (0.16 g, 3 mmol) and 2-chlorophenyl hydrazine hydrochloride (0.535 g, 3 mmol) in 10 mL H2O was heated at reflux for 4 hours. The reaction mixture was cooled and the solids formed were filtered washed with H2O and dried to give 0.296 mg of the intermediate hydrazone. The hydrazone was heated to 200° C. under argon for 2 hours. The residue was purified by flash chromatography (hexane-EtOAc, 2:1) to give 0.055 g of product as a tan solid

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solids formed
  5. filtrationwere filtered
  6. washwashed with H2O
  7. customdried

Sources & evidence

ORD record
ord-524bf29a9254423bab70153953cee6b6
Source dataset
uspto-grants-2007_07
Patent number
US07241791B2

Reaction notes

Loading…