Nitric Acid → 4-Bromo-7-hydroxy-6-nitro-2,3-dihydro-1H-inden-1-one

HRID 883186Notes

Reaction equation

HRID 883186 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:12].C(OC(=O)C)(=O)C.[N+:20]([O-])([OH:22])=[O:21]>C(O)(=O)C>[Br:1][C:2]1[CH:10]=[C:9]([N+:20]([O-:22])=[O:21])[C:8]([OH:11])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:12]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 37180504-Bromo-7-hydroxy-1-indanone

Product 1

HCID 577812334-Bromo-7-hydroxy-6-nitro-2,3-dihydro-1H-inden-1-oneYield 81.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

4-Bromo-7-hydroxyindan-1-one (3.06 g, 13.5 mmol) was suspended in acetic acid (20 mL), and acetic anhydride (1.66 mL, 17.6 mmol) and fuming nitric acid (838 μL, 20.2 mmol) dissolved in acetic acid (10 mL) were added. The mixture was stirred at room temperature for 3 hr. The solvent was evaporated under reduced pressure and the precipitated yellow crystals were collected by filtration to give the title compound (2.98 g, yield 79%).

Workup

  1. additionwere added
  2. customThe solvent was evaporated under reduced pressure
  3. filtrationthe precipitated yellow crystals were collected by filtration

Sources & evidence

ORD record
ord-13bb3efcd7fd450bb282932202cdd711
Source dataset
uspto-grants-2012_08
Patent number
US08236837B2

Reaction notes

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