The important role of 2-(4-Oxocyclohexyl)isoindoline-1,3-dione

According to the analysis of related databases, 104618-32-8, the application of this compound in the production field has become more and more popular.

Related Products of 104618-32-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 104618-32-8 as follows.

A solution of N-(4-oxocyclohexyl)phthalimide (14, 5.00 g, 21 mmol, 1 eq.) and 4-methoxyphenylhydrazine hydrochloride (3.59 g, 21 mmol, 1 eq.) in dry ethanol (100 mL) was heated at reflux for 2.5 h. After cooling down to room temperature, the precipitate was filtrated off and washed with ethanol 96% (3 * 10 mL). The solid was dried under reduced pressure and freeze-dried overnight. Rf = 0.66 (cyclohexane/ethyl acetate/dimethylethylamine 5:5:0.2). Colorless solid, mp 222-223 C, yield 6.88 g (97%). Purity (HPLC): 84.1% (tR = 22.2 min). C21H18N2O3 (346.4 g/mol). Exact mass (APCI): m/z = 347.1389 (calcd. 347.1390 for C21H19N2O3 [M + H+]). 1H NMR (400 MHz, DMSO-D6): delta (ppm) = 2.03-2.11 (m, 1H, 2-H), 2.67 (tt, J = 12.3/6.4 Hz, 1H, 2-H), 2.80-2.98 (m, 3H, 1-CH2, 4-H), 3.20-3.28 (m, 1H, 4-H), 3.71 (s, 3H, OCH3), 4.43-4.52 (m, 1H, 3-H), 6.65 (dd, J = 8.7/2.4 Hz, 1H, 7-H), 6.82 (d, J = 2.4 Hz, 1H, 5-H), 7.15 (d, J = 8.7 Hz, 1H, 8-H), 7.84-7.91 (m, 4H, 4-Hphth, 5-Hphth, 6-Hphth, 7-Hphth), 10.61 (s, 1H, NH). 13C NMR (101 MHz, DMSO-D6): delta (ppm) = 22.6 (1C, C-1), 24.7 (1C, C-4), 26.5 (1C, C-2), 47.8 (1C, C-3), 55.3 (1C, OCH3), 99.7 (1C, C-5), 106.3 (1C, C-4a), 109.9 (1C, C-7), 111.2 (1C, C-8), 123.0 (2C, C-4phth, C-7phth), 127.2 (1C, C-4b), 131.3 (1C, C-8a), 131.5 (2C, C-3aphth, C-7aphth), 134.2 (1C, C-9a), 134.4 (2C, C-5phth, C-6phth), 153.0 (1C, C-6), 167.9 (2C, C=O). FTIR (neat): ? (cm-1) = 3425 (w, N-H), 3379 (w, C-H, arom), 2924 (w, C-H, aliph), 1697 (s, C=O), 1597 (w, C-C, arom).

According to the analysis of related databases, 104618-32-8, the application of this compound in the production field has become more and more popular.