Pyridine → 1H-Inden-1-one, 5-bromo-2,3-dihydro-, O-methyloxime

HRID 1268912Notes

Reaction equation

HRID 1268912 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=O)[CH2:6][CH2:5]2.Cl.[O:13]([NH2:15])[CH3:14].N1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(O)C>[CH3:14][O:13][N:15]=[C:7]1[C:8]2[C:4](=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 5206955-Bromo-1-indanoneHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 730128401H-Inden-1-one, 5-bromo-2,3-dihydro-, O-methyloximeYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-bromo-indanone (100 g, 0.474 mol) in ethanol (650 ml) under argon was added methoxylamine hydrochloride (198 g, 2.38 mol) and pyridine (125 ml). The mixture was refluxed for 2.5 hours, cooled to room temperature and poured into saturated aqueous sodium hydrogen carbonate solution. The mixture was then extracted with ethyl acetate and the organic phase dried (sodium sulphate) and then concentrated in vacuo. The crude material was recrystallised from isopropanol to furnish the title compound, (110 g, 97%), as a brown solid; 1HMR (CDCl3) 7.52 (1H, d, J 8.3 Hz), 7.43 (1H, d, J 1 Hz), 7.35 (1H, dd, J 8.3, 1Hz), 3.97 (3H, s), 2.99 (2H, m), 2.99 (2H, m), 2.85 (2H, m).

Workup

  1. temperatureThe mixture was refluxed for 2.5 hours
  2. extractionThe mixture was then extracted with ethyl acetate
  3. dry with materialthe organic phase dried (sodium sulphate)
  4. concentrationconcentrated in vacuo
  5. customThe crude material was recrystallised from isopropanol

Sources & evidence

ORD record
ord-7a8727fe23a74fce8e013a964c3a33d9
Source dataset
uspto-grants-2007_04
Patent number
US07199137B2

Reaction notes

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