446292-04-2

Basic information

• Product Name: 4-(4-NITROPHENYL)MORPHOLIN-3-ONE
• Synonyms: 4-(4-NITROPHENYL)MORPHOLIN-3-ONE;3-Morpholinone, 4-(4-nitrophenyl)-;4-(4-Nitrophenyl)-3-Morpholinone;4-(3-Oxo-4-morpholinyl)nitrobenzene;4-(4-Nitrophenyl)-3-oxomorpholine;4-(3-Oxo-4-morpholinyl)nitrobenzene 4-(4-Nitrophenyl)-3-oxomorpholine
• CAS NO: 446292-04-2
• Molecular Formula: C₁₀H₁₀N₂O₄
• Molecular Weight: 222.2
• EINECS: 1308068-626-2
• Product Categories: Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 446292-04-2.mol
• Article Data: 34

Chemical Properties

• Boiling Point: 516.802 °C at 760 mmHg
• Flash Point: 266.352 °C
• Appearance: /
• Density: 1.397
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: -4.12±0.20(Predicted)
• CAS DataBase Reference: 4-(4-NITROPHENYL)MORPHOLIN-3-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-NITROPHENYL)MORPHOLIN-3-ONE(446292-04-2)
• EPA Substance Registry System: 4-(4-NITROPHENYL)MORPHOLIN-3-ONE(446292-04-2)

Safety Data

• Safety Statements: 24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 446292-04-2(Hazardous Substances Data)

Usage

Description

4-(4-Nitrophenyl)morpholin-3-one is an organic compound that serves as a reagent in the synthesis of various morpholine-based pharmaceuticals. It is a yellow solid with chemical properties that make it suitable for use in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
4-(4-Nitrophenyl)morpholin-3-one is used as a reagent for the preparation of various morpholine-based pharmaceuticals. Its role in the synthesis process is crucial for creating a range of medications that can be used to treat different health conditions.
Used in the Synthesis of Rivaroxaban Impurity 52:
4-(4-Nitrophenyl)morpholin-3-one is also utilized in the synthesis of Rivaroxaban Impurity 52, which is an important compound in the development and manufacturing of Rivaroxaban, a medication used to treat and prevent blood clots. 4-(4-nitrophenyl)morpholin-3-one's involvement in the production of this impurity highlights its significance in the pharmaceutical sector.

InChI:InChI=1/C10H10N2O4/c13-10-7-16-6-5-11(10)8-1-3-9(4-2-8)12(14)15/h1-4H,5-7H2

Upstream product

• 109-11-5 morpholine-3-one 
• 350-46-9 4-Fluoronitrobenzene 
• 75-21-8 oxirane 
• 79-04-9 chloroacetyl chloride 
• 62-53-3 aniline 
• 636-98-6 p-nitrobenzene iodide 
• 10389-51-2 1-morpholino-4-nitrobenzene 
• 100-00-5 4-chlorobenzonitrile 
• 100463-96-5 bromoethyloxyacetonitrile 
• 100-01-6 4-nitro-aniline 
• 31250-08-5 2-chloroethyl cyanomethyl ether 
• 55851-35-9 N-(2-bromoethyl)-4-nitrobenzenamine 
• 1965-55-5 4-nitro-N-2-chloroethylaniline 
• 103-84-4 Acetanilid 

Downstream Products

• 438056-69-0 4-(4-aminophenyl)morpholin-3-one 
• 697284-64-3 (R)-{3-methyl-1-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-butyl}-carbamic acid tert-butyl ester 
• 366789-02-8 Rivaroxaban 
• 446292-10-0 4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one 
• 446292-07-5 2-((2S)-2-hydroxy-3-{[4-(3-oxomorpholin-4-yl)phenyl]amino}propyl)-1H-isoindole-1,3(2H)-dione 

Relevant articles and documents

Synthesis, Characterization, and Biological Evolution of New Pyrazole Derivatives of 4-(4-Aminophenyl)morpholin-3-one through Ugi Reaction

A new heterocyclic library was synthesized using multicomponent reactions (MCRs). A green strategy during which a set of molecules with an excellent diversity is generated with a minimum of synthetic effort, time, and by-products formation. This new series prepared using the Ugi MCRs in which aldehyde, amine, acid, and isocyanide reacts to make α-bisamide. During this work, we practice the Ugi reaction to synthesize an extremely functionalized heterocyclic library which was characterized and tested for biological evaluation. This innovative synthetic route involves for pyrazole derivatives of 4-(4-aminophenyl)morpholin-3-one by Ugi four component reaction and methanol as a solvent in good yield and high purity. All the produced compounds of library were characterized using 1H-NMR, IR, and mass spectroscopic methods.

Synthesis method of 4-(4-aminophenyl)-3-morpholone

The invention provides a synthesis method of 4-(4-aminophenyl)-3-morpholone. The method comprises the following steps: condensing p-halonitrobenzene and morpholine which are used as starting materials to generate 4-(4-nitrophenyl) morpholine, oxidizing 4-(4-nitrophenyl) morpholine by taking a halite or chlorine dioxide as an oxidizing agent and controlling the pH value of a reaction system to be less than 7 to generate 4-(4-nitrophenyl)-3-morpholone, and finally reducing to generate the target product 4-(4-aminophenyl)-3-morpholone. The synthesis method of 4-(4-aminophenyl)-3-morpholinone provided by the invention has the advantages of greenness, high efficiency, easiness in industrial application and the like.

PROCESS FOR THE PREPARATION OF 4-(4-AMINOPHENYL)MORPHOLIN-3-ONE

The field of this invention relates to a novel process, suitable for industrial scale manufacture, for the preparation of 4-(4-aminophenyl)morpholin-3-one of Formula (I), the key intermediate of rivaroxaban according to the scheme. In the process 2-(2-chloroethoxy)ethanol of Formula (XI) is oxidized to 2-(2-chloroethoxy)- acetic acid with aqueous sodium- or calcium-hypochlorite and a catalyst. The 2-(2~ chloroethoxy)acetic acid of Formula (X) is reacted with 4-nitro-aniline of Formula (VII) with phenylboronic acid catalyst. Then the 2-(2-chloroetoxy)-N-(4-nitrophenyl)acetamide of Formula (IX) is transformed to 4-(4-nitrophenyl)morpholin-3-one of Formula (IV) in a ?one- pot" procedure. The 4-(4-nitrophenyl)morpholin-3-one of Formula (IV) is hydrogenated to get 4-(4-aminophenyl)morpholin-3-one of Formula (I).