2-Cyclohexen-1-one → 3-(5-Nitro-1H-indol-3-yl)cyclohexan-1-one

HRID 1186272Notes

Reaction equation

HRID 1186272 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[C:13]1(=[O:19])[CH2:18][CH2:17][CH2:16][CH:15]=[CH:14]1>CC#N>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH:15]1[CH2:16][CH2:17][CH2:18][C:13](=[O:19])[CH2:14]1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 135942-Cyclohexen-1-oneHCID 225235-Nitroindole

Product 1

HCID 573848053-(5-Nitro-1H-indol-3-yl)cyclohexan-1-oneYield 41%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-nitroindole (4.00 g, 25.61 mmol) in dry MeCN (5.00 mL) was added cyclohex-2-enone (7.40 mL, 76.83 mmol) and Bi(NO3)3 (0.12 g, 0.26 mmol) and the mixture stirred overnight at room temperature. The solvent then was evaporated and the crude was purified by column chromatography (50% Hexane:50% EtOAc) to obtain the title compound (2.70 g, 41%) as a yellow solid. 1H-NMR (CDCl3) δ 1.81-2.09 (m, 3H), 2.26-2.34 (m, 1H), 2.37-2.55 (m, 2H), 2.65 (dd, 1H, J=9.9, 12.9 Hz), 2.77-2.85 (m, 1H), 3.47-3.56 (m, 1H), 7.15 (d, 1H, J=2.1 Hz), 7.41 (d, 1H, J=9.0 Hz), 8.12 (dd, 1H, J=2.1, 9.0 Hz), 8.51 (s, 1H), 8.59 (d, 1H, J=2.1 Hz); EI-MS (m/z, %) 258 (M+, 100).

Workup

  1. customThe solvent then was evaporated
  2. customthe crude was purified by column chromatography (50% Hexane:50% EtOAc)

Sources & evidence

ORD record
ord-37402550b0594fa68ba42d9cbf25147f
Source dataset
uspto-grants-2014_03
Patent number
US08673909B2

Reaction notes

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