Hydrochloric Acid → 6-fluoroindan-1-one O-methyloxime

HRID 2240391Notes

Reaction equation

HRID 2240391 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=O)=[CH:4][CH:3]=1.Cl.[O:13]([NH2:15])[CH3:14]>N1C=CC=CC=1.C(OC(=O)C)C>[CH3:14][O:13][N:15]=[C:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:10]=2)[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 4113O-MethylhydroxylamineHCID 15194646-Fluoro-1-indanone

Product 1

HCID 860822766-fluoroindan-1-one O-methyloximeYield 81%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-fluoro-indan-1-one (0.5 g, 3.33 mmol) in pyridine (10 ml) was added the HCl salt of methoxylamine (0.31 g, 3.66 mmol) and stirred at room temperature for overnight. The reaction mixture was diluted with ethylacetate (50 ml), acidified with 3N HCl, and washed with 1N HCl, water and brine sequentially. The solution was dried (Na2SO4) and concentrated to yield 0.48 g (81%) of product. MS (ESI+) m/z 180 (M+H)+;

Workup

  1. washwashed with 1N HCl, water and brine sequentially
  2. dry with materialThe solution was dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-11155f70b66245d5a5169aafe54ef6d8
Source dataset
uspto-grants-2010_05
Patent number
US07723367B2

Reaction notes

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