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

HRID 1040691Notes

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-fcdb7f791cb149bc9cb5fda8b84962cd
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552186B2

Reaction notes

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