5-Methoxyindan-1-one → 5-Methoxyindan-1-one oxime

HRID 1881793Notes

Reaction equation

HRID 1881793 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH2:7][CH2:6]2.Cl.[NH2:14][OH:15].C([O-])(=O)C.[Na+]>O.CO.C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[N:14][OH:15])[CH2:7][CH2:6]2

Participants

7

Reactant 3

HCID 787875-Methoxyindan-1-oneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 2881895-Methoxyindan-1-one oxime

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

5-Methoxy-2,3-dihydromden-1-one (Ig, 6.17 mmol) was added to a solution of hydroxylamine HCl (730 mg, 10.5 mmol) in 10 ml of water. The mixture was brought up to 70° C. and a solution of sodium acetate (1.4 g, 16.7 mmol) in 7 mL of H2O, 14 ml of MeOH, 3 ml of THF was added. After stirring for 1.5 h at 70° C., 10 ml of H2O was added to produce a precipitate and the suspension was allowed to stir for 2 h. The precipitate was collected by filtration to give 5-methoxy-2,3-dihydroinden-1-one oxime almost quantitatively and was used in the next step without further purification. The oxime (0.5 g, 2.82 mmol) was dissolved in MeOH and a catalytic amount of Raney nickel and 25 mL of ammonia solution in MeOH (7N) was added. The reaction was stirred at r.t. overnight under H2. The slurry was filtered over celite and concentrated in vacuo, diluted with EtOAc, washed with water and brine, dried over MgSO4, filtered, and concentrated in vacuo to give the crude title amine (yield, 45%). The crude amine was used without further purification.

Workup

  1. customwas brought up to 70° C.
  2. customto produce a precipitate
  3. stirringto stir for 2 h
  4. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-b5acdce661774062b0c643ae8e90ecdd
Source dataset
uspto-grants-2012_11
Patent number
US08318947B2

Reaction notes

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