Nitric Acid → 2-Nitro-8,9-dihydro-5H-benzo[7]annulen-7(6H)-one

HRID 1687001Notes

Reaction equation

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

Participants

Conditions

Temperature: -35 °C

Procedure

A flask containing 90% nitric acid was cooled to at −35° C. using an acetonitrile-dry ice bath. 5,6,8,9-Tetrahydro-benzocyclohepten-7-one (0.5 g, 0.003 mol) was added in portions over 30 minutes. The mixture was warmed slightly to at −20° C. for 1.5 h until all of the material was dissolved. The mixture was poured over ice and water and the resulting precipitate was collected by filtration and washed with water. The solid was dried at under vacuum overnight to give a tan solid (0.58, 78%), 2-nitro-5,6,8,9-tetrahydrobenzocyclohepten-7-one. 1H NMR (400 MHz, DMSO-d6) δ 8.12 (s, 1H), 8.09 (d, 1H, J=8.4 Hz), 7.40 (d, 1H, J=8.4 Hz), 3.03 (m, 4H), 2.65 (m, 4H),

Workup

temperatureThe mixture was warmed slightly to at −20° C. for 1.5 h until all of the material
dissolutionwas dissolved
filtrationthe resulting precipitate was collected by filtration
washwashed with water
customThe solid was dried at under vacuum overnight

Sources & evidence

ORD record: ord-2642a5d0b1cb4970a975b05b8779667f
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148391B2

Reaction notes

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