4-CYANOQUINOLINE

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.Step A: Preparation of 4-cyanoquinolineTo a solution of N-methylpyrrolidinone (100 mL) and CuCN (21.5 g, 240 mmol) was added 4-bromoquinoline (25.0 g, 120 mmol) in one portion with vigorous stirring under nitrogen. The reaction was heated to 180 °C for 3 hours. The reaction mixture was allowed to cool, and then added to water (300 mL). The crude solid product was filtered and dried in a vacuum oven overnight to give the title product (8.03 g).‘HNMR(CDC13) ö 7.73-7.81 (m, 2 H) 7.89 (ddd, J=8.47, 7.01, 1.34 Hz, 1 H) 8.11-8.34 (m, 2 H) 9.06 (d, J4.39 Hz, 1 H).General procedure: To a solution of the corresponding N-heterocycles (10.0 mmol) in CH2Cl2 (20 mL), m-chloroperoxybenzoic acid (m-CPBA, 20.0 mmol, 2.0 equiv) was added at 0 C. The reaction mixture was allowed to stir at room temperature for 12 h. Then saturated aqueous NaHCO3 (20 mL) was added. The aqueous was extracted with CH2Cl2 (10 mL x 3) and the combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with EtOAc/n-hexene or EtOAc/MeOH to afford desired N-oxides.General procedure: The Pd/AC was synthesized as per our reported procedure using Pd(NO3)2 solution (Chanotiya et al. 2016). Surface area was measured using Beckman Coulter SA3100 surface area analyser. Surface area of the Pd/AC catalyst is 380 sqm/g. Mettler Toledo TGA/DSC1 Stare system was used for the thermo-gravimetric analysis (Dhiman et al. 2017). The TGA-DTG analysis of this catalyst inferred that there was no major weight loss in the temperature range of 50-800oC. Therefore the catalyst was stable in this temperature range mentioned above. TEM CM 200 of Philips make used for the transmission electron microscope analysis with operating voltage 20-200 kv of 2.4Ao resolution. Isolated QCN was further reduced using Pd/Ac catalyst at different temperature and solvent systems (Table S3). In another approach, the reduced products having similar structural relationship with QCN, so this compound is further confirmed through derivatization.

Molecular Weight:154.17
XLogP3:2
Hydrogen Bond Acceptor Count:2
Exact Mass:154.053098200
Monoisotopic Mass:154.053098200
Topological Polar Surface Area:36.7
Heavy Atom Count:12
Complexity:203
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes