Category: 874-90-8

Reference of 874-90-8, These common heterocyclic compound, 874-90-8, name is 4-Methoxybenzonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Bis(4-methoxyphenyl)methammine (1) was prepared according to the procedure described in Pickert et al., (1973) Organic Syntheses Coll. Fpp520-522 and Dejaegher et al., (2002) Synlett 113-115. Magnesium (0.76 g) was suspended in 30 mL dry THF in a flame-dried 3-neck round-bottomed flask equipped with a stir bar. Some drops of 4-bromoanisole were added, and to initiate the reaction, a crystal of iodine was added and the solution heated to a gentle reflux (-6O0C). Once the color of the iodine had disappeared, the remaining l-bromo-4- methoxybenzene (3.9 mL) in 8 mL THF was added. The mixture was refluxed for 45 minutes. After cooling to RT, 2.5 g of p-methoxybenzonitrile in dry THF was added over 20 minutes and reacted for 6 h under reflux. The reaction mixture was cooled and 4.5 mL of methanol added to quench the reaction. After stirring for 20 minutes, it was concentrated to remove THF, redissolved in CH2Cl2 and quickly washed with water in a separatory funnel to remove Mg salts. The CH2Cl2 layer was dried over MgSO4, concentrated, redissolved in a minimal amount of dichloromethane and diethyl ether added to precipitate white shiny crystals of Bis(4- methoxyphenyl)methanimine (4.01 g, 59% yield). It is worthy of mention that the preparation of this diarylketimine was simple and efficient resulting in crystals without any additional lengthy purification steps such as distillation or chromatography which contributes to the simpler glycosylation chemistry. Rf = 0.32 (60% EtOAc: hexanes), m.p. = 128-129 0C, 1H NMR (CDCl3, 500 MHz) d 3.84 (6H, s), 6.90 (4H, d, J= 9.0 Hz), 7.52 (4H, d, J= 8.5 Hz), 8.95 (NH, broad) ; 13C NMR (CDCl3, 500 MHz) d 55.3 (2CH3O), 113.4 (4CH), 129.98 (4CH), 132.1(2C, q), 161.1 (2C- O, q), and 176.9 (C=N).

Statistics shows that 4-Methoxybenzonitrile is playing an increasingly important role. we look forward to future research findings about 874-90-8.

Reference:
Patent; THE ARIZONA BOARD OF REGENTS ON BEHALF OF THE UNIVERSITY OF ARIZONA; WO2007/55698; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 874-90-8, These common heterocyclic compound, 874-90-8, name is 4-Methoxybenzonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Bis(4-methoxyphenyl)methammine (1) was prepared according to the procedure described in Pickert et al., (1973) Organic Syntheses Coll. Fpp520-522 and Dejaegher et al., (2002) Synlett 113-115. Magnesium (0.76 g) was suspended in 30 mL dry THF in a flame-dried 3-neck round-bottomed flask equipped with a stir bar. Some drops of 4-bromoanisole were added, and to initiate the reaction, a crystal of iodine was added and the solution heated to a gentle reflux (-6O0C). Once the color of the iodine had disappeared, the remaining l-bromo-4- methoxybenzene (3.9 mL) in 8 mL THF was added. The mixture was refluxed for 45 minutes. After cooling to RT, 2.5 g of p-methoxybenzonitrile in dry THF was added over 20 minutes and reacted for 6 h under reflux. The reaction mixture was cooled and 4.5 mL of methanol added to quench the reaction. After stirring for 20 minutes, it was concentrated to remove THF, redissolved in CH2Cl2 and quickly washed with water in a separatory funnel to remove Mg salts. The CH2Cl2 layer was dried over MgSO4, concentrated, redissolved in a minimal amount of dichloromethane and diethyl ether added to precipitate white shiny crystals of Bis(4- methoxyphenyl)methanimine (4.01 g, 59% yield). It is worthy of mention that the preparation of this diarylketimine was simple and efficient resulting in crystals without any additional lengthy purification steps such as distillation or chromatography which contributes to the simpler glycosylation chemistry. Rf = 0.32 (60% EtOAc: hexanes), m.p. = 128-129 0C, 1H NMR (CDCl3, 500 MHz) d 3.84 (6H, s), 6.90 (4H, d, J= 9.0 Hz), 7.52 (4H, d, J= 8.5 Hz), 8.95 (NH, broad) ; 13C NMR (CDCl3, 500 MHz) d 55.3 (2CH3O), 113.4 (4CH), 129.98 (4CH), 132.1(2C, q), 161.1 (2C- O, q), and 176.9 (C=N).

Statistics shows that 4-Methoxybenzonitrile is playing an increasingly important role. we look forward to future research findings about 874-90-8.

Reference:
Patent; THE ARIZONA BOARD OF REGENTS ON BEHALF OF THE UNIVERSITY OF ARIZONA; WO2007/55698; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 874-90-8, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 874-90-8, name is 4-Methoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Aryl nitrile 4a-e (15.0mmol) was dissolved in ethanol (25mL) in a round-bottom two-necked balloon, under magnetic stirring, and hydroxylamine hydrochloride (2.085g, 30mmol) and aqueous NaOH (2 equiv, 10mL) were added to the mixture. The mixture was stirred at room temperature for 15-24h, monitoring the reaction by TLC. Then, the solvent was removed under rotary evaporation and water (20mL) was added to the crude mixture. The mixture was extracted with ethyl acetate (3¡Á20mL) and the organic layer was dried over anhydrous MgSO4 and filtered. The solvent was removed by rotary evaporation and the product was recrystallized from chloroform – hexane.

The chemical industry reduces the impact on the environment during synthesis 4-Methoxybenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Mayer, Joao C.P.; Sauer, Andre C.; Iglesias, Bernardo A.; Acunha, Thiago V.; Back, Davi F.; Rodrigues, Oscar E.D.; Dornelles, Luciano; Journal of Organometallic Chemistry; vol. 841; (2017); p. 1 – 11;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts