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

HRID 1035040Notes

Reaction equation

HRID 1035040 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-d003efa43b434edb959210a10a813a38
Source dataset
uspto-grants-2013_10
Patent number
US08546374B2

Reaction notes

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