Category: 550-89-0

Synthetic Route of 550-89-0, These common heterocyclic compound, 550-89-0, name is Phenazine-1-carboxamide, 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.

Example 1: Synthesis of 1-amino-phenazineA solution of sodium methanolate (25% in MeOH, 24.6 ml, 107 mmol) in 100 ml MeOH was cooled to -78C and a solution of bromine (2.10 ml, 40.9 mmol) in 10.0 ml MeOH was added over a period of 2 min. Under further cooling the solution was first stirred 5 min followed by the addition of phenazine- 1-carboxamide (4.00 g, 17.9 mmol) in 200 ml dry methanol and 400 ml dry THF over a period of 1 h via dropping funnel. After the complete addition a clear orange solution was obtained that was warmed to room temperature and further stirred 2 h at 55C. Following the mixture was cooled down to room temperature and stirred further 72 h. After evaporating under reduced pressure the residue was dissolved in methanol (300 ml) and aqueous NaOH (40%, 150 ml) and refluxed for 4 h at 90C. Subsequently the solution was cooled down to 0C and set to pH 8.5 with concentrated HC1, obtain- ing a dark red suspension. After concentrating to about 200 ml under reduced pressure 500 ml water was added. The mixture was extracted three times with CHC13. The combined organic layers were dried over Na2S04 and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (n-hexane/ethyl acetate, 80:20 -> 75:25) obtaining 2.86 g (82%) of the title compound as dark red solid.

The synthetic route of 550-89-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROCHE DIAGNOSTICS GMBH; F. HOFFMANN-LA ROCHE AG; ROCHE DIAGNOSTICS OPERATIONS, INC.; HEINDL, Dieter; NORTMEYER, Christine; GEBAUER, Peter; HUNT DU VALL, Stacy; BAUER-ESPINDOLA, Klaus Andreas; WO2015/158645; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

550-89-0, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 550-89-0, name is Phenazine-1-carboxamide, A new synthetic method of this compound is introduced below.

Synthesis of the specific process: phenazine-1-carboxamide hydrolysis under acidic conditions to produce phenazine-1-carboxylic acid;Take 20mmol of phenazine-1-carboxylic acid (0.4577g) and 200ml of thionyl chloride was added to a 500ml round bottom flask, the installation of a reflux reaction device (using anhydrous calcium chloride drying tube), magnetic stirring, reflux reaction 6h, After cooling, the thionyl chloride was removed by rotary evaporation to obtain the intermediate phenazine-1-carbonyl chloride, which was used for the next reaction without purification;The obtained phenazine-1-carboxylic acid chloride was dissolved in 200ml of dry dichloromethane (DCM), added into a 500ml dry round bottom flask, protected by nitrogen, magnetically stirred, placed in an ice-water bath and cooled, and then 11.15 ml triethylamine (80 mmol, 4 equiv.) and2.367 g of 3-methoxy-1-propylamine(20mmol, 1equiv.) After the addition of ice water bath was removed at room temperature for 14h, intermittent sampling,The reaction was monitored by TLC. After DCM was removed by rotary evaporation, the reaction mixture was extracted three times and extracted with 450 ml of liquid (ethyl acetate and H 2 O in a volume ratio of 2: 1) each time. The combined organic phases were dried over anhydrous sodium sulfate for 12 h, filtered, EA washed the solid sodium sulfate, rotary steam, in order to transform the compoundProduct 15-1, 1.4883 g, 22.93% yield.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Hunan Agricultural University; Zhang Ya; Liao Xiaolan; Liu Shuangqing; Xiang Yaqin; (7 pag.)CN106922679; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics