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