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

HRID 1593415Notes

Reaction equation

HRID 1593415 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 97.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-bromoindan-1-one (100 g, 0.47 mol) in ethanol (650 ml) under argon was added methoxylamine hydrochloride (198 g, 2.38 mol) and pyridine (125 ml). The mixture was heated under reflux for 2.5 hours, cooled to room temperature and poured into saturated aqueous sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate and the organic phase dried and concentrated in vacuo. The crude material was recrystallised from isopropanol to afford the title compound (110 g, 97%); 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 heated
  2. temperatureunder reflux for 2.5 hours
  3. extractionThe mixture was extracted with ethyl acetate
  4. customthe organic phase dried
  5. concentrationconcentrated in vacuo
  6. customThe crude material was recrystallised from isopropanol

Sources & evidence

ORD record
ord-f116889aff854720adbcd82167c4da6d
Source dataset
uspto-grants-2007_11
Patent number
US07297694B2

Reaction notes

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