Hydroxyamine hydrochloride → 4-methoxy-2,3-dihydro-1H-inden-1-one oxime

HRID 384973

Reaction equation

HRID 384973 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=O.[NH2:13][OH:14].Cl.C([O-])(=O)C.[Na+]>CO>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=[N:13][OH:14]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 45474914-methoxy-2,3-dihydro-1H-inden-1-one

Product 1

HCID 766564544-methoxy-2,3-dihydro-1H-inden-1-one oximeYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-methoxy-2,3-dihydro-1H-inden-1-one (1.0 g, 1.0 eq.) in 25 ml MeOH was added NH2OH.HCl (0.493 g, 1.15 eq.) and sodium acetate (0.597 g, 1.18 eq.). The resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with 100 ml ice-water. The white precipitate was collected by filtration, washed with 3×20 ml water and dried in vacuo to afford 1.08 g (yield 99%) 4-methoxy-2,3-dihydro-1H-inden-1-one oxime which was used to next step without further purification.

Workup

  1. filtrationThe white precipitate was collected by filtration
  2. washwashed with 3×20 ml water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-d3a87c1c72994cb09db54a91dd7ee20b
Source dataset
uspto-grants-2013_02
Patent number
US08367836B2

Linked notes

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