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

HRID 340662Notes

Reaction equation

HRID 340662 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-1124d3474cab404aa625d5fbd57a2ec6
Source dataset
uspto-grants-2014_11
Patent number
US08895591B2

Reaction notes

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