Ethanol → HCID 86762607, compound

HRID 2407463Notes

Reaction equation

HRID 2407463 reaction equation
Cl.[C:2]1([NH:8]N)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][CH:11]([C:20](=O)[CH3:21])[CH2:12][CH2:13][CH2:14][CH2:15][S:16]([OH:19])(=[O:18])=[O:17].O.[CH2:24](O)[CH3:25]>[Cl-].[Cl-].[Zn+2]>[CH3:10][C:11]1([CH2:12][CH2:13][CH2:14][CH2:15][S:16]([O-:19])(=[O:18])=[O:17])[C:3]2[C:4]3[CH:10]=[CH:11][CH:20]=[CH:21][C:5]=3[CH:6]=[CH:7][C:2]=2[N+:8]([C:25]2[CH:24]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:20]1[CH3:21]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 60962Phenylhydrazine hydrochlorideHCID 579033515-Methyl-6-oxoheptanesulfonic acid

Product 1

HCID 86762607HCID 86762607, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

N-(2-Naphtyl), N-phenylhydrazine hydrochloride (19.51 mmol, 5.28 g), 5-methyl-6-oxoheptanesulfonic acid (17.18 mmol, 3.70 g) and anhydrous ZnCl2 (17.18 mmol, 2.34 g) in absolute ethanol (30 ml) were stirred at room temperature for 30 min, then at 80° C. for 2 h. the reaction progress was checked by TLC (10% H2O in CH2CN). After completion the reaction was cooled down and the solvent removed under vacuum. The residue was dissolved in DCM and purified by flash column on silica-gel. Yield: 3.06 g, 42%.

Workup

  1. temperatureAfter completion the reaction was cooled down
  2. customthe solvent removed under vacuum
  3. dissolutionThe residue was dissolved in DCM
  4. custompurified by flash column on silica-gel

Sources & evidence

ORD record
ord-91f3d3bd9aa2461eac610688e98927f1
Source dataset
uspto-grants-2014_08
Patent number
US08809551B1

Reaction notes

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