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[ CAS No. 153-78-6 ]

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Chemical Structure| 153-78-6
Chemical Structure| 153-78-6
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CAS No. :153-78-6 MDL No. :MFCD00001125
Formula : C13H11N Boiling Point : 358.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :181.23 g/mol Pubchem ID :1539
Synonyms :

1. 2-Aminofluorene

Safety of [ 153-78-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H351-H361 Packing Group:N/A
GHS Pictogram:

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  • Upstream synthesis route of [ 153-78-6 ]
  • Downstream synthetic route of [ 153-78-6 ]

[ 153-78-6 ] Synthesis Path-Upstream   1~13

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YieldReaction ConditionsOperation in experiment
99% With sodium tetrahydroborate In methanol; water at 0 - 50℃; for 2 h; General procedure: A mixture of nitroarene (1 mmol), SS-Pd (2 molpercent Pd) and sodium borohydride (3 mmol) were taken in a 25 ml round bottomed flask. 3 ml of MeOH:H2O (3:7) was added to the mixture by a syringe at 0 oC in stirring condition. After 10 minutes the reaction mixture was heated to 50 oC. Progress of the reaction was monitored by TLC. On completion, the reaction mixture was extracted with ethylacetate and dried over anhydrous Na2SO4. Evaporation of the combined organic layer and followed by column chromatography over silica gel (60-120 mesh) afforded desired corresponding amines.
99% With hydrogen; triethylamine In ethanol; water at 110℃; for 20 h; Autoclave General procedure: In a 4 ml_ reaction glass vial fitted with a septum cap containing a magnetic stirring bar, Co-Co3O4Chit-700 (10 mg, 3.4 molpercent Co), the nitroarenes (0.5 mmol, 1 .0 equiv.) and triethylamine (35 μΙ_, 0.25 mmol, 0.5 equiv.) were added to a solvent mixture of EtOH/H20 (3/1 , 2 ml_). The reaction vial was then placed into a 300 ml_ autoclave, flashed with hydrogen five times and finally pressurized to 40 bar. The reaction mixture was stirred for appropriate time at 1 10 °C. After cooling the reaction mixture to room temperature, the autoclave was slowly depressurized. The crude reaction mixture was filtered through a pipette fitted with a cotton bed and the solvent was evaporated under reduced pressure. The crude products were purified by passing through a silica plug (eluent: ethyl acetate) to give pure aniline derivatives after removal of solvent. The following compounds may be prepared from the respective nitroarenes using the catalyst of the invention:
97% With sodium tetrahydroborate In ethanol; water at 25℃; for 4 h; General procedure: SAC (300mg) and NaBH4 (4.0mmol) were added to a solution of nitroarenes (1.0mmol) in EtOH/water (1/1) (20ml). The reaction mixture was stirred for 4h at the temperature indicated in Table3. At the end of the reaction, the catalyst was removed by filtering and the filtrate was extracted with 3×70ml EtOAc. The combined organic layers were dried over MgSO4 and concentrated in a vacuum.
97% With iron; ammonium chloride In ethanol; water at 85℃; for 4 h; Reflux; Inert atmosphere A mixture of 2-nitro-9H-fluorene (2.0 g, 9.5 mmol), iron powder (1.0 g, 18.7 mmol), andNH4Cl (0.75 g, 12.46 mmol) was refluxed in aqueous ethanol(75 mL of alcohol and 25 mL of water) at 85 °C for 4 h under argon atmosphere. The reaction was monitored by TLC (solvent EtOAc–hexane 2:3). After completion of the reaction, theresulting mixture was treated with 50 mL of saturated aqueoussodium bicarbonate solution and filtered off. The transparentfiltrate was concentrated in vacuum in order to remove theorganic solvent. The residue was filtered off to yield compound4(1.67g, 97percent) as transparent plates. The crude product wasused directly in the next step. 1H NMR (CDCl3, 400 MHz) δ7.66 (d, J= 7.6 Hz, 1H), 7.60 (d, J= 8.0 Hz, 1H), 7.50 (d, J =7.2 Hz, 1H), 7.35 (td, J= 7.6 and J= 0.8 Hz, 1H), 7.22 (td, J=7.6 and J= 1.2, 1H), 6.9 (br s, 1H), 6.73 (dd, J= 8.0 and J= 2.4Hz, 1H), 3.84 (s, 2H), 3.70 (br s, 2H, NH2) ppm; 13C NMR(CDCl3, 100 MHz) δ145.75, 145.16, 142.27, 142.15, 133.01,126.64, 125.09, 124.76, 120.67, 118.6, 113.98, 111.82, 36.83ppm.
96% With sodium tetrahydroborate In ethanol; water at 20℃; for 1.5 h; General procedure: TAPEHA-Pd (0.015 g) was added to a solution of nitroarenes (1.0 mmol) in EtOH/water (1/1) (20 mL). After NaBH4 (4.0 mmol) was slowly added to the mixture, the color of the reaction mixture turned gradually black in a few minutes, resulting in the formation of palladium nanoparticles (TAPEHA-PdNPs). 42 After being stirredfor 1.5 h at room temperature and atmospheric pressure, the catalyst was removed by ltering and the fitrate was extracted with 3 30 mL of EtOAc. The combined organic layers were dried over MgSO4 and concentrated in a vacuum.
93% at 80℃; for 0.0833333 h; Microwave irradiation A mixture of 1j (100 mg, 0.81 mmol), hydrazine hydrate (121.5mg, 2.43 mmol), and SS-Rh (370 mg, 2 molpercent Rh) were taken in an oven dried reaction tube equipped with screw cap. 0.5 ml of PEG-400 was added into the reaction mixture. The reaction was then irradiated in a microwave apparatus at 80°C , 80 W for 10 min with a pressure of 80 Psi. After cooling to ambient temperature in the microwave cavity the reaction mixture was extracted with ethyl acetate (3x2 ml) and water (1ml). The combined organic layer wasdried over anhydrous Na2SO4 and the solvent was removed under reduced pressure and after purificationwith silica gel column chromatography (Hexane: EtOAc::95:5) 2j as brown powder (80 mg, 93percent), m.p.124-125°C. 1H and 13C NMR spectra has beencompared with our previously reported study.3 ESI-MS: m/z calc. for (M+H)+ C13H11N182.2405 and obsd.182.0631
78% With calcium chloride; zinc In ethanol Reduction of 2-nitrofluorene with Zn/CaCl2 in ethanol gave 2-aminofluorene (17) in 78percent yield.
62% With 5%-palladium/activated carbon; hydrazine hydrate In ethanol at 0.5℃; for 3.5 h; Reflux In a two-necked round-bottomed flask (500 mL) equipped with a reflux condenser and a dropping funnel, a suspension of 2-nitro-9H-fluorene (10.12 g, 48 mmol), palladium on carbon 5percent (5 g), and ethanol (250 mL) was prepared.
The mixture was heated, and while being stirred magnetically, hydrazine hydrate 85percent (35 mL) in ethanol (50 mL) was added dropwise over a 1.5 h period through the dropping funnel while maintaining the temperature at about 50 °C.
The reaction mixture was then refluxed for 2 h and filtered while hot.
On cooling, the filtrate gave light yellow colored crystals of the title diamine compound, which was recrystallized from ethanol and dried under vacuum to give 5.4 g (62percent yield) (Scheme1).
mp 129-134 °C. 1H NMR (400 MHz, CDCl3), δ, ppm: 7.66 (1H, d, J = 7.6 Hz), 7.59 (1H, d, J = 8 Hz), 7.49 (1H, d, J = 7.6 Hz), 7.36-7.32 (1H, m), 7.22 (1H, ddd, J = 1.2 Hz, J = 7.6 Hz), 6.91 (1H, t, J = 0.4 Hz), 6.74 (1H, dd, J = 2 Hz, J = 8 Hz), 3.83 (2H, S), 3.76 (2H, S, NH2).
13C NMR (100 MHz, CDCl3), δ, ppm: 145.74, 145.16, 142.26, 142.14, 133, 126.63, 125.08, 124.75, 120.66, 118.58, 113.97, and 111.81.
The mass spectrum show peak at m/z = 181.1 corresponding to compound F2 (Figs. S3-S4).
92 %Chromat. With carbon monoxide; water In tetrahydrofuran at 125℃; for 24 h; Inert atmosphere; Autoclave General procedure: Into a reaction glass vial fitted with a magnetic stirring bar anda septum cap penetrated with a syringe needle was added theCo3O4/NGrC-catalyst (2 molpercent, 3 wtpercent Co-phenanthroline oncarbon, 20 mg) followed by the nitro arene (0.5 mmol), theinternal standard (hexadecane, 100 μL), THF (2 mL), and H2O(200 μL). The reaction vial was then placed into a 300 mL autoclave.The autoclave was flushed twice with nitrogen, pressurized with CO at 30 bar pressure. Finally, the autoclave was usedat 60 bar by adding nitrogen and placed into an aluminiumblock, which was preheated at 125 °C. After 24 h the autoclavewas placed into a water bath and cooled to r.t. Finally, theremaining gas was discharged, and the samples were removedfrom the autoclave, diluted with EtOAc and analyzed by GC. Todetermine the yield of isolated products, the general procedurewas scaled up by the factor of two, and no internal standard wasadded. After the reaction was completed, the catalyst was filteredoff, and the filtrate was concentrated and purified by silicagel column chromatography (n-heptane–EtOAc mixtures) togive the corresponding anilines.
99 %Chromat. With 4-amino-phenol; triethylamine In ethanol; water at 110℃; for 9 h; Autoclave General procedure: In an 8mL glass vial fitted with a magnetic stirring bar and a septum cap, the catalyst (the amount depends on the catalyst) was added followed by the nitroarene (0.5mmol), the internal standard (hexadecane, 20mg) and the solvent (2mL). A needle was inserted in the septum cap, which allows dihydrogen to enter. The vials (up to 7) were placed into a 300mL steel Parr autoclave which was flushed twice with dihydrogen at 20bar and then pressurized to 50bar. Then the autoclave was placed into an aluminum block pre-heated at 110°C. At the end of the reaction, the autoclave was quickly cooled down at room temperature with an ice bath and vented. Finally, the samples were removed from the autoclave, diluted with a suitable solvent, filtered using a Pasteur pipette filled with Celite® (6cm pad) and analyzed by GC using n-hexadecane as an internal standard. Control experiments showed that the position of the vial inside the autoclave is not influential. The same outcome was obtained when the reaction was repeated by moving a vial from a peripheral to a central position.

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YieldReaction ConditionsOperation in experiment
43%
Stage #1: With hydrogenchloride; sodium nitrite In water at 0℃; for 1 h;
Stage #2: With sodium iodide In water at 20℃; for 4 h;
General procedure: To a solution of corresponding amine (1 eq) in 18percent HCl (12 mL)was added NaNO2 (1 M in H2O, 1.5 eq) at 0 C. The mixture wasstirred at 0 C for 1 h, and then NaI (2 M in H2O, 2 eq) was added.After the mixture was stirred at room temperature for 4 h, Na2SO3(4 eq) was added. The suspension was filtered to give the desiredproducts 10-12. 6.1.4.1
2-Iodo-9H-fluorene (10)
Yellow solid (43percent); 1H NMR (400 MHz, CDCl3) δ 7.89 (s, 1H), 7.76 (d, J = 7.6 Hz, 1H), 7.70 (d, J = 8.0 Hz, 1H), 7.54 (d, J = 8.0 Hz, 2H), 7.41-7.31 (m, 2H), 3.88 (s, 2H).
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