As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 41175-50-2, name is 1,2,3,5,6,7-Hexahydropyrido[3,2,1-ij]quinolin-8-ol, molecular formula is C12H15NO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Recommanded Product: 1,2,3,5,6,7-Hexahydropyrido[3,2,1-ij]quinolin-8-ol
General procedure: To a solution of aldehyde 4a (200 mg, 0.391 mmol) in propionic acid was added 8-hydroxyjulolidine (148 mg, 0.782 mmol, 2 equiv) and PTSA (7 mg, 0.039 mmol, 0.1 equiv). The solution was protected from light and stirred at room temperature overnight. To the brown mixture was added a solution of chloranil (95 mg, 0.391 mmol, 1 equiv) in DCM (10 mL), the reaction turned dark and was allowed to stir overnight at room temperature. The dark purple solution was evaporated to dryness, dissolved in DCM and washed with a saturated solution of NaHCO3. The organic phase was dried over MgSO4, filtrated, and evaporated. The crude was purified by column chromatography on silica gel (gradient of 100% DCM to 9/1 DCM/methanol) to obtain 222 mg of 5a (61%) as a purple solid after lyophilization (from dioxane/water: 1/1). 1H NMR (300 MHz, CDCl3): delta 8.85 (s, 1H, NH), 8.54-8.52 (m, 1H, HPy), 7.88 (s, 1H, CH triazole), 7.68 (t, J=7.3 Hz, 1H, HPy), 7.24 (t, J=6.2 Hz, 1H, HPy), 7.13 (d, J=7.8 Hz, 1H, HPy), 6.99 (d, J=8.0 Hz, 1H, Ha), 6.93 (s, 2H, H7), 6.85-6.82 (m, 2H, Hb, Hc), 5.59 (s, 2H, NCH2Py), 4.77 (s, 2H, OCH2CON), 4.60 (d, J=5.6 Hz, 2H, CH2NCO), 4.28 (s, 4H, CH2COOMe), 3.76 (s, 6H, OMe), 3.52 (dt, J=10.9, 5.5 Hz, 8H, H1, H4), 3.03 (t, J=6.3 Hz, 4H, H6), 2.84-2.67 (m, 4H, H3), 2.15-2.07 (m, 4H, H5), 2.00-1.97 (m, 4H, H2). 13C NMR (75 MHz, CDCl3): delta 172.20 (CO ester), 168.31 (CO amide), 154.89, 154.67, 152.48, 151.21, 149.82, 149.36 (CHPy), 145.90, 141.17, 138.00 (CHPy), 127.33 (C7), 126.22, 123.86, 123.77 (Cb or Cc), 123.61 (CH triazole), 123.56 (CHPy), 122.62 (CHPy), 119.42 (Ca), 115.83 (Cb or Cc), 113.05, 105.37, 68.55 (OCH2CON), 55.33 (NCH2Py), 53.91 (CH2COOMe), 52.34 (OMe), 51.20 (C1 or C4), 50.66 (C1 or C4), 35.28 (CH2NCO), 27.79 (C3), 20.93 (C2), 20.18 (C6), 20.04 (C5). MS (ES+), calcd for C48H51N8O7+ [M]+ 851.4, found 851.4. HRMS (ES+), calcd for C48H51N8O7+ [M]+ 851.3875, found 851.3901.
With the rapid development of chemical substances, we look forward to future research findings about 41175-50-2.
Reference:
Article; Collot, Mayeul; Lasoroski, Aurelie; Zamaleeva, Alsu I.; Feltz, Anne; Vuilleumier, Rodolphe; Mallet, Jean-Maurice; Tetrahedron; vol. 69; 48; (2013); p. 10482 – 10487;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts