Hydroxyamine hydrochloride → 5-Bromo-2,3-dihydro-1H-inden-1-one Oxime

HRID 473082Notes

Reaction equation

HRID 473082 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.[NH2:13][OH:14]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[N:13]/[OH:14])/[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 5206955-Bromo-1-indanone

Product 1

HCID 594615935-Bromo-2,3-dihydro-1H-inden-1-one OximeYield 88.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-bromo-2,3-dihydro-1H-inden-1-one (25 g, 118 mmol) and hydroxylamine hydrochloride (12.35 g, 178 mmol) were heated in Ethanol (150 mL) for 5 hours with stirring. The solvent was evaporated in vacuo and remaining solid partitioned between H2O and EtOAc. The organic layer was separated and washed with brine (2×), dried on Na2SO4 and solvent evaporated in vacuo to afford the title compound as a light brown solid (23.6 g, 87%). MS (ESI): m/z [M+H]+ 227.0

Workup

  1. customThe solvent was evaporated in vacuo
  2. custompartitioned between H2O and EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine (2×)
  5. customdried on Na2SO4 and solvent
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-121a97ab78944121ab84896d2a3cee3e
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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