2,6-Pyridinedicarbonitrile

white to off-white powder

The liquid ammonia (0.5 ml) and acetonitrile (50 ml) at -40 ° C in cold bath, adding pyridine -2, 6-dicarboxylic acid (1.67g), to 0 °C, batch by adding phosphorus pentachloride (4g), is omitted, stirring the mixture at room temperature for 2 hours, the response finishes, concentrated under reduced pressure, the residue is dissolved with methylene chloride, washed with saturated sodium bicarbonate to neutral, anhydrous magnesium sulphate dried, concentrated, precipitated solid, the resulting solid is recrystallized with isopropyl alcohol, to obtain white crystal of 2, 6-di-cyano pyridine (1.13g). The yield is 88percent.General procedure: to a solution of 2-pyridinecarbaldehyde 1 (54 mg, 0.5 mmol) and ammonium acetate (385mg, 5.0 mmol) in MeCN )6ml), was added trimethylphenylammonium tribromide (376 mg, 1.0 mmol) at room temperature. after stirring for 21 h at rt, the reaction mixture was treated with 0.5 M aq Na2S2O3(10 ml), 1.0 M NaHCO3 )15 ml) and extracted with EtOAc (60 mL). The organic layer was washed with 0.5 M Na2S2O3 and successively washed with saturated aq.NaCl, and dried over MgSO4.General procedure: Aryl bromide (6.0 mmol), K4[Fe(CN)6]·3H2O (2.4 mmol), Na2CO3 (6.0 mmol) and Pd(OAc)2 catalyst (0.2 molpercent relative tothe aryl bromide) were mixed in NMP (12 mL) in a 25‐mLflame‐dried double‐neck round‐bottom flask and heated withstirring at 130 °C under argon. The progress of the reaction wasmonitored by GC‐MS. At the end of the reaction, the mixturewas cooled to room temperature. Samples were quenched withH2O (or with sat. NH4Cl when pyridines were used as substrates), and extracted with EtOAc (25 mL × 3). The organiclayer was washed with water (15 mL × 3) and 5percent NH3·H2O (15mL × 2), and then dried over Na2SO4. Evaporation of the solventleft the crude product, which was further purified by columnchromatography over silica gel (60–120 mesh) eluting withpetroleum ether/ethyl acetate to afford the pure aryl nitrile.1, 4‐Dicyanobenzene (1b, DCB). 1H NMR (CDCl3, 400 MHz): δ= 7.80 (s, 4H); 13C NMR (101 MHz, CDCl3): δ = 132.81, 117.00, 116.76.General procedure: Sodium (5 mg) was added to dry methanol (10 mL) followed by the appropriate heteroaromatic nitrile (1.24/0.62 mmol) and the resulting solution was stirred at 25 C until TLC (SiO2; EtOAc) or GC/MS showed total conversion of the nitrile into the corresponding imidate (usually 1-4 h). (1R, 2S, 3R)-Camphordiamine dihydrochloride (299 mg, 1.24 mmol), triethylamine (0.5 mL) and acetic acid (3 drops) were then added and the resulting solution was stirred at 40 C for 12 h. The solvent was evaporated in vacuo and the crude product was purified by column chromatography (SiO2; EtOAc/MeOH 2:1) to afford pure product.A 100 cm3 ask was lled with Bistetrazolate pyridine was synthesized from

Molecular Weight:129.12
XLogP3:1
Hydrogen Bond Acceptor Count:3
Exact Mass:129.032697108
Monoisotopic Mass:129.032697108
Topological Polar Surface Area:60.5
Heavy Atom Count:10
Complexity:181
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes