Nitric Acid → 3-Nitro-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-one
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
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
- temperaturecooling
- filtrationThe precipitates were collected by filtration
- dissolutiondissolved into ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over magnesium sulfate
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-89576a314cf546c2abe5c9ccb7df30f7
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06495546B1
Reaction notes
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