4-Aminobenzeneacetonitrile

yellow to brown crystalline powder, crystals

Compound 1 (10 g, 61.67 mmol) was dissolved in methanol (50 mL).Add 10percent Pd/C (1.0g), Replace the reaction system four times with H2, Stir at room temperature overnight in H2 environment (0.5 MPa).TLC analysis, the reaction was complete, and the reaction solution was filtered through celite.The filtrate was concentrated under reduced pressure to give 8.08g of Compound 2, The yield was 99.1percent.VI 5-0 g (30 mmol) was taken, Dissolved in 25 ml of ethanol, 8 g (150 mmol) NH4Cl, Dissolved in 40 ml of water, Was added to a three-necked flask, 5. 05 g (90 mmol) of iron powder was added, Mechanical stirring, Reflux 2h.Filter in addition to iron powder, CH2CV washing filter cake, Extraction with CH2C12, Saturated sodium chloride, Dried over anhydrous sodium sulfate, filter, Evaporated to dryness 3. 86 g of solid, The yield was 97.5percentStep 2 4-Aminophenylacetonitrile (3): Method A: To a solution of (274 gm, 1.69 moles) 4-nitrophenylacetonitrile (2) in 2740 ml of ethyl acetate, wet 10percent palladium on charcoal (27.4 gm) was added at 20-25°C under nitrogen atmosphere. Reaction mixture was subjected to hydrogenation at 50-60 PSI for 3-4 hrs. After completion of reaction, as revealed from TLC, reaction mixture was filtered and washed with 250 ml of ethyl acetate. Filtrate on evaporation gave 213 gm of 4-aminophenylacetonitrile (3) as orange colored solid. Dry weight: 213 gm (96percent). 1H NMR(CDC13 and 400MHZ): 53.57 (2H, s), 3.74 (2H, s), 6.63 (2H, d), 7.05 (2H, d)Example-4 The following example illustrates the hydrogenation of various nitroaromatics as mentioned in Table 4. The hydrogenation of exemplary nitroaromatics was conducted under the following conditions. The procedure was similar to that for biphasic reactions [reaction numbers 7- 10, Table 2] Reaction conditions: Pressure: 400 psi; Temperature: 423K; Aqueous phase: 9x10-5 m3 ; Organic phase consists of neat substrate; catalyst FeS04. 7H20 : 7. 2x10-5 mol ; Fe: EDTANa2 1: 5; conversion in all cases was complete ; TOF calculated as mols of nitro compound converted per mol of Fe, .sect. based on GC analysis. Table 4 Reaction No Substrate Substrate Yield of TOF (mols) corresponding hr~' amine percent 16 Nitrobenzelle 0. 090 98. 5 529 17 2-nitrotoluene 0. 0849 98. 75 457 18 2, 4-dinitrotoluene 0. 056 84. 63 134 19 4-nitrochlorobenzene 0.0635 96. 2 434 20 3-nitrochlorobenzene 0. 0635 99 400 21 2-nitrotoluene 0. 0849 98. 75 462 22 2-nitroanisole 0. 0820 89. 19 450 23 2-nitroaniline 0.0725 98. 2 116 24 4-nitrobenzoic acid 0.0598 85.8 393 25 4-nitro acetophenone 0.06 99 208 26 4-nitro benzylnitrile 0. 061 90 99General procedure: To a screw top vial (5 mL) under N2 containing freshly distilled toluene (0.6 mL) were successively added an aromatic nitro compound (0.60 mmol), InI3 (14.9 mg, 0.030 mmol), and TMDS (318 μL, 1.80 mmol). After the vial was sealed with a cap that contained a PTFE septum, the mixture was stirred at 60 °C (bath temperature), and monitored via TLC analysis. Sat. aq NaHCO3 solution (5 mL) was added to the resultant mixture, which was then extracted with EtOAc (3 × 6 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (n-hexane–EtOAc, 9:1 to 4:1) to afford the corresponding aniline derivative.

Used in the preparation of succinic acid, pentanediol, tetrahydrofuran, pyran, etc.; also used as a solvent for paints, resins and greases; used as a lubricant and dispersant in the printing and dyeing industry; pharmaceutical intermediates; decolorizing agent and deodorizing medicine Agents; also used as raw materials for organic synthesis of plasticizers, herbicides, pesticides, etc.

Molecular Weight:132.16
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:132.068748264
Monoisotopic Mass:132.068748264
Topological Polar Surface Area:49.8
Heavy Atom Count:10
Complexity:137
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes