2-Acetyl-1,2,3,4-tetrahydronaphthalen-1-one → HCID 58948768, compound

HRID 598757Notes

Reaction equation

HRID 598757 reaction equation
[C:1]([CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=O)(=O)[CH3:2].Cl.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][NH2:25])=[CH:20][CH:19]=1>C(O)C.O>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:5]3[C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=4[CH2:12][CH2:13][C:4]=3[C:1]([CH3:2])=[N:25]2)=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 865272-Acetyl-1,2,3,4-tetrahydronaphthalen-1-oneHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 58948768HCID 58948768, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-acetyl-1-tetralone (329 mg, 1.75 mmol) in ethanol (12 mL) was added 4-methoxyphenyl hydrazine hydrochloride. The stirred suspension was heated to 80° C. overnight. The reaction was cooled to room temperature and diluted with water (100 mL) and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water, 10% NaOH, 10% HCl, brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue purified on silica gel using a 5% EtOAc to 25% EtOAc in hexane gradient (yield 396 mg). LC-MS (C19H18N2O calculated 290) m/z 291 (M+H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe combined organic layers were washed with water, 10% NaOH, 10% HCl, brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customthe residue purified on silica gel using a 5% EtOAc to 25% EtOAc in hexane gradient (yield 396 mg)

Sources & evidence

ORD record
ord-a16ac41c67564c8082e094af060e9a2c
Source dataset
uspto-grants-2011_03
Patent number
US07897634B2

Reaction notes

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