Methanol → HCID 10607526, compound

HRID 1420675Notes

Reaction equation

HRID 1420675 reaction equation
[C:1]1(=O)[C:12]2=[C:13]3[C:8](=[CH:9][CH:10]=[CH:11]2)[CH:7]=[CH:6][CH:5]=[C:4]3[CH2:3][CH2:2]1.Cl.[NH2:16]O.CO.C([O-])(=O)C.[Na+]>O>[CH:1]1([NH2:16])[C:12]2=[C:13]3[C:8](=[CH:9][CH:10]=[CH:11]2)[CH:7]=[CH:6][CH:5]=[C:4]3[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 6027812,3-Dihydro-1H-phenalen-1-one

Product 1

HCID 10607526HCID 10607526, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a stirred mixture of 2,3-dihydro-phenalen-1-one (1.32 g, 7.24 mmol), hydroxylamine hydrochloride (0.85 g, 12.2 mmol) and water (6 ml) was added dropwise at 75° C. MeOH (7.5 ml) and afterwards a solution of sodium acetate (2.58 g, 19.0 mmol) in water (4 ml). Stirring was continued over a period of 1.5, h, water (20 ml) was added and after cooling (ice bath) the solid was collected by filtration. After drying in vacuo the crude product was dissolved in 3.5 N NH3 /MeOH (100 ml) and hydrogenated over Raney-Nickel (0.5 g, washed with MeOH) at RT for 17h. The catalyst was filtered off, the solution evaporated in vacuo and the residue purified by column chromatography on silica gel (dichloromethane/MeOH 9:1) to yield (RS)-2,3-dihydro-1H-phenalen-1-yl-amine (0.95 g) as a brown oil.

Workup

  1. additionwas added dropwise at 75° C
  2. additionwas added
  3. temperatureafter cooling (ice bath) the solid
  4. filtrationwas collected by filtration
  5. dry with materialAfter drying in vacuo the crude product
  6. dissolutionwas dissolved in 3.5 N NH3 /MeOH (100 ml) and hydrogenated over Raney-Nickel (0.5 g, washed with MeOH) at RT for 17h
  7. filtrationThe catalyst was filtered off
  8. customthe solution evaporated in vacuo
  9. customthe residue purified by column chromatography on silica gel (dichloromethane/MeOH 9:1)

Sources & evidence

ORD record
ord-e061e39338044ee19378bc581f681886
Source dataset
uspto-grants-2000_06
Patent number
US06071925

Reaction notes

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