Methane → 9,9-Dioctyl-9H-fluorene-2,7-diamine

HRID 2241066Notes

Reaction equation

HRID 2241066 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][C:10]([N+:17]([O-])=O)=[CH:11][CH:12]=3)[C:7]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:6]=2[CH:5]=1)([O-])=O.[H][H].C.CC(=O)OCC>C(O)C.O1CCCC1.[Pd].C(Cl)(Cl)Cl>[NH2:1][C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][C:10]([NH2:17])=[CH:11][CH:12]=3)[C:7]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:6]=2[CH:5]=1

Participants

9

Reactant 4

HCID 297MethaneHCID 8857Ethyl AcetateHCID 593060062,7-Dinitro-9,9-dioctyl-9H-fluoreneHCID 178418361HCID 178418361, compound

Product 1

HCID 593060059,9-Dioctyl-9H-fluorene-2,7-diamine

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

2,7-Dinitro-9,9-dioctylfluorene (27.84 g, 57.93 mmol) was dissolved in absolute ethanol (90 mL) and tetrahydrofuran (THF, 50 mL). Palladium on carbon (5%, 0.5 g) was subsequently added. The mixture was placed on a Parr hydrogenator and shaken under 40 psi of hydrogen for 4 hrs. at room temperature. The mixture was filtered through CELITE® and the solvent removed by rotary evaporation to afford a red-brown liquid. The crude product was dissolved in CHCl3 and stirred with decolorizing charcoal for 1 hr. at room temperature. The solution was filtered and the solvent removed by rotary evaporation to give a red liquid that slowly solidified into needle-like crystals (mp 58-63° C.). Yield=22.36 g (91.76%). 1H NMR (300 MHz, CDCl3) δ 0.7 (m, 4H), 0.8 (t, 6H), 1.0-1.3 (m, 20H), 1.9 (m, 4H), 3.6 (s, 4H), 6.6 (m, 4H), 7.3 (d, 2H) ppm. 13C NMR (75 MHz, CDCl3) δ 15, 23, 24, 30, 30, 31, 32, 41, 55, 111, 114, 119, 134, 145, 152 ppm. EA calcd. for C29H46N2: % C, 82.80; % H, 10.54; % N, 6.66. Found: % C, 82.29; % H, 10.06; % N, 6.73.

Workup

  1. customat room temperature
  2. filtrationThe mixture was filtered through CELITE®
  3. customthe solvent removed by rotary evaporation
  4. customto afford a red-brown liquid
  5. customat room temperature
  6. filtrationThe solution was filtered
  7. customthe solvent removed by rotary evaporation
  8. customto give a red liquid that

Sources & evidence

ORD record
ord-6365517c32564279af4630d9c103dd15
Source dataset
uspto-grants-2010_05
Patent number
US07723464B2

Reaction notes

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