881-70-9

Basic information

• Product Name: N-(3,4-dimethoxyphenyl)ethanamide
• Synonyms: N-(3,4-dimethoxyphenyl)acetamide;N-(3,4-dimethoxyphenyl)ethanamide;2,2-dimethoxy-N-phenylacetamide
• CAS NO: 881-70-9
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.21512
• Mol File: 881-70-9.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 359.7°C at 760 mmHg
• Flash Point: 171.4°C
• Appearance: /
• Density: 1.144g/cm³
• Vapor Pressure: 2.33E-05mmHg at 25°C
• Refractive Index: 1.544
• CAS DataBase Reference: N-(3,4-dimethoxyphenyl)ethanamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3,4-dimethoxyphenyl)ethanamide(881-70-9)
• EPA Substance Registry System: N-(3,4-dimethoxyphenyl)ethanamide(881-70-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 881-70-9(Hazardous Substances Data)

Usage

Uses

N-(3,4-Dimethoxyphenyl)acetamide is an intermediate used in the synthesis of 5,6-Orthoquinone Primaquine-d6 Hydrobromide (O697512), which is an isotope labeled compound of 5,6-Orthoquinone Primaquine (O697510). 5,6-Orthoquinone Primaquine is used in the study of the differential pharmacological and toxicological properties of primaquine enantiomers. Primaquine is currently the only approved drug for the treatment and radical cure of Plasmodium vivax malaria.

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 5814, 1994 DOI: 10.1021/jo00098a050

InChI:InChI=1/C10H13NO3/c1-7(12)11-8-4-5-9(13-2)10(6-8)14-3/h4-6H,1-3H3,(H,11,12)

Upstream product

• 6315-89-5 3,4-dimethoxyaniline 
• 91-16-7 1,2-dimethoxybenzene 
• 64-19-7 acetic acid 
• 10352-44-0 4'-(methylthio)acetanilide 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 93-91-4 1-phenylbutan-1,3-dione 
• 75-05-8 acetonitrile 
• 67-56-1 methanol 
• 51-66-1 4-methoxyacetanilide 
• 79-24-3 Nitroethane 
• 75-36-5 acetyl chloride 
• 62-44-2 4-ethoxyacetanilide 

Downstream Products

• 32829-09-7 2-chloro-4,5-dimethoxyaniline 
• 6315-89-5 3,4-dimethoxyaniline 
• 1381862-03-8 N-acetyl-3-methoxy-p-benzoquinone imine dimethyl acetal 
• 64701-03-7 3,4,4-trimethoxycyclohexa-2,5-dienone 
• 121638-95-7 N-[4,5-Dimethoxy-2-(thiophene-2-carbonyl)-phenyl]-acetamide 
• 101382-56-3 6,7-Dimethoxy-2-oxo-1,2-dihydro-quinoline-3-carbaldehyde 
• 106835-45-4 3-Amino-6,7-dimethoxy-1H-pyrazolo<3,4-b>quinoline 
• 93299-56-0 2-chloro-6,7-dimethoxy-3-quinolinecarbonitrile 

Relevant articles and documents

Zinc(II)-Catalyzed Synthesis of Secondary Amides from Ketones via Beckmann Rearrangement Using Hydroxylamine-O-sulfonic Acid in Aqueous Media

A zinc(II)-catalyzed single-step protocol for the Beckmann rearrangement using hydroxylamine-O-sulfonic acid (HOSA) as the nitrogen source in water was developed. This direct method efficiently produces secondary amides under open atmosphere in a pure form after basic aqueous workup. It isenvironmentally benign and operationally simple.

Cu(OTf) 2 -Catalyzed Beckmann Rearrangement of Ketones Using Hydroxylamine- O -sulfonic Acid (HOSA)

The Beckmann rearrangement (BKR) of ketones to secondary amides often requires harsh reaction conditions that limit its practicality and scope. Herein, the Cu(OTf) 2 -catalyzed BKR of ketones under mild reaction conditions using hydroxylamine- O -sulfonic acid (HOSA), a commercial water soluble aminating agent, is described. This method is compatible with most functional groups and directly provides the desired amides in good to excellent yields.

General rhodium-catalyzed oxidative cross-coupling reactions between anilines: Synthesis of unsymmetrical 2,2′-diaminobiaryls

Described herein is a dual chelation-assisted RhCl3-catalyzed oxidative C-H/C-H cross-coupling reaction of aniline derivatives. The highlight of this methodology is the chemo- and regioselective cross-coupling between electronically similar substrates, which represents a highly challenging task in oxidative Ar-H/Ar-H cross-coupling reactions. Furthermore, this Cp?-free catalytic reaction tolerates a range of functional groups and requires only a low molar ratio of coupling partners. These features expedite the synthesis of unsymmetrical 2,2′-diaminobiaryls.