1-Indanone, 4-bromo- → HCID 72392271, compound

HRID 2175206Notes

Reaction equation

HRID 2175206 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=O.Cl.[NH2:13][OH:14]>CO>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[N:13][OH:14]

Participants

4

Reactant 2

HCID 987131-Indanone, 4-bromo-HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 72392271HCID 72392271, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-bromo-2,3-dihydro-1H-inden-1-one (3.00 g, 14.21 mmol) in MeOH (40 mL) was added hydroxylamine hydrochloride (3.95 g, 56.9 mmol). The resulting mixture was refluxed for 1 h and concentrated in vacuo. The resulting residue was partitioned between DCM and 50% saturated NaHCO3, and stirred vigorously for 20 min. The organic layer was separated, dried over anhydrous Na2SO4, filtered and concentrated to afford the title compound (3.18 g, 99% yield) as a pale yellow solid. LCMS, [M+H]+=226.0.

Workup

  1. temperatureThe resulting mixture was refluxed for 1 h
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was partitioned between DCM and 50% saturated NaHCO3
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-039edd99a58244709bf84e0bba6a5a69
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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