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

HRID 912633Notes

Reaction equation

HRID 912633 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.[CH3:13][O:14][NH2:15]>N1C=CC=CC=1>[CH3:13][O:14][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

4

Reactant 2

HCID 5206955-Bromo-1-indanoneHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 730128401H-Inden-1-one, 5-bromo-2,3-dihydro-, O-methyloxime

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Bromo-1-indanone and O-methylhydroxylamine hydrochloride were combined in pyridine and stirred at ambient temperature for 16 hours. The mixture was concentrated under reduced pressure and the residue was suspended in diethyl ether. The suspension was filtered and the filter cake was washed with diethyl ether. The filtrate was washed with water, 1N HCl, water, and concentrated to provide the title compound. 1H NMR (300 MHz, d6-DMSO) 7.63 (m, 2H), 7.48 (m, 2H), 3.90 (s, 3H), 3.00 (m, 2H), 2.80 (m, 2H); MS (DCI/NH3) m/e 240 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. filtrationThe suspension was filtered
  3. washthe filter cake was washed with diethyl ether
  4. washThe filtrate was washed with water, 1N HCl, water
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dcecd7c7bb4a484bb80e87262ddfe601
Source dataset
uspto-grants-2011_09
Patent number
US08026256B2

Reaction notes

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