Hydrochloric Acid → 6-Fluoro-5-methoxy-indan-1,2-dione 2-oxime

HRID 2100725Notes

Reaction equation

HRID 2100725 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][C:3]=1[O:12][CH3:13].Cl.C([O:19][N:20]=O)CCC>CO>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[N:20][OH:19])[C:8]2=[O:11])=[CH:4][C:3]=1[O:12][CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10996Butyl nitriteHCID 552971586-Fluoro-5-methoxy-2,3-dihydro-1H-inden-1-one

Product 1

HCID 766087786-Fluoro-5-methoxy-indan-1,2-dione 2-oximeYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-Fluoro-5-methoxy-indan-1-one (4.8 g) in 65 ml of MeOH was added 2.7 ml of concentrated HCl, then a solution of n-butylnitrite (3.47 ml) at room temperature. The resulting mixture was stirred for 2 hrs, the precipitate was collected and dried to yield the product as a white solid (3.9 g, 70% yield). LC-MS: m/e 210 (MH+)

Workup

  1. customat room temperature
  2. customthe precipitate was collected
  3. customdried

Sources & evidence

ORD record
ord-bf9c5b68338a4a45a22a26ae19da139e
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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