Nitric Acid → 1-[1-(4-Nitrophenyl)tricyclo[3.3.1.03,7]non-3-yl]ethanone

HRID 1015515Notes

Reaction equation

HRID 1015515 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.O.[C:11]1([C:17]23[CH2:25][CH:21]4[CH2:22][CH:23]([CH2:24]2)[C:19]([C:26](=[O:28])[CH3:27])([CH2:20]4)[CH2:18]3)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>[N+](C)([O-])=O>[N+:1]([C:14]1[CH:15]=[CH:16][C:11]([C:17]23[CH2:25][CH:21]4[CH2:22][CH:23]([CH2:24]2)[C:19]([C:26](=[O:28])[CH3:27])([CH2:20]4)[CH2:18]3)=[CH:12][CH:13]=1)([O-:4])=[O:2]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 593749561-(2-Phenylhexahydro-2,5-methanopentalen-3a-yl)ethanone

Product 1

HCID 670178651-[1-(4-Nitrophenyl)tricyclo[3.3.1.03,7]non-3-yl]ethanoneYield 88%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

Nitration mixture (1 mL) [the nitration mixture was prepared by mixing of 10.5 g of nitric acid (d 1.375 at 22° C.), 180.0 g of conc. sulphuric acid (d 1.84 at 22° C.), and 16 g of H2O) was added drop wise to a stirred solution of 1-(1-phenyltricyclo[3.3.1.03,7]non-3-yl)ethanone (240 mg, 1.0 mmol) obtained in preparation 1, in nitromethane (4 mL) at 0° C. After stirring for 2 h, the reaction mixture was poured into ice cold water and extracted with EtOAc, the combined organic layers were washed with brine and dried over Na2SO4. The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography to obtain 1-[1-(4-nitrophenyl)tricyclo[3.3.1.03,7]non-3-yl]ethanone as an off-white solid (250 mg) in 88% yield. M.R: 61.3-66.6° C. m/z (M+1) 286; IR cm−1 2953, 1697, 1598, 1519, 1217, 1110, 852, 768. 1H NMR (CDCl3) 300 MHz δ 8.17 (d, J=8.7 Hz, 2H), 7.43 (d, J=8.7 Hz, 2H), 2.87-2.80 (m, 1H), 2.61-2.55 (m, 1H), 2.34-2.26 (m, 1H), 2.23 (s, 3H), 2.13-1.98 (m, 4H), 1.90-1.71 (m, 5H).

Workup

  1. additionthe reaction mixture was poured into ice cold water
  2. extractionextracted with EtOAc
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated under reduced pressure
  6. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-a114b17567584e76a6945a9f3bfe8cd9
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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