Nitric Acid → 3-Nitro-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-one

HRID 1351863Notes

Reaction equation

HRID 1351863 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH:5]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:15](=[O:16])[C:9]=2[CH:8]=[CH:7][CH:6]=1>>[N+:1]([C:7]1[CH:6]=[CH:5][C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:15](=[O:16])[C:9]=2[CH:8]=1)([O-:4])=[O:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 70003Benzosuberone

Product 1

HCID 3444873-Nitro-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-one

Procedure

Under nitrogen, to fuming nitric acid (60 ml) was added 6,7,8,9-tetrahydrobenzocyclohepten-5-one (20 g) on ice-cooling, and the mixture was stirred at the same temperature for 1 hour. The resulting mixture was poured into ice water (200 ml). The precipitates were collected by filtration and dissolved into ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo to afford 3-nitro-6,7,8,9-tetrahydrobenzocyclohepten-5-one (14.87 g).

Workup

  1. temperaturecooling
  2. filtrationThe precipitates were collected by filtration
  3. dissolutiondissolved into ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-b173208306ea4986b4b490bab3a4376b
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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