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

HRID 1180530Notes

Reaction equation

HRID 1180530 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 (Na2SO4) and then concentrated in vacuo. The crude material was recrystallised from isopropanol to furnish the title compound, (110 g, 97%), as a brown solid; 1H NMR (CDCl3) 7.52 (1H, d, J 8.3 Hz), 7.43 (1H, d, J 1 Hz), 7.35 (1H, dd, J 8.3, 1 Hz), 3.97 (3H, s), 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 (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude material was recrystallised from isopropanol

Sources & evidence

ORD record
ord-7684189b1cfc4cea986bede0fa582aaa
Source dataset
uspto-grants-2007_10
Patent number
US07282500B2

Reaction notes

Loading…