214476-09-2

Basic information

• Product Name: 4-Chloro-3-cyano-7-ethoxy-6-nitroquinoline
• Synonyms: 4-Chloro-3-cyano-7-ethoxy-6-nitroquinoline;4-Chloro-7-ethoxy-6-nitro-3-quinolinecarbonitrile;3-Quinolinecarbonitrile, 4-chloro-7-ethoxy-6-nitro-;4-chloro-7-ethoxy-6-nitroquinoline-3-carbonitrile
• CAS NO: 214476-09-2
• Molecular Formula: C₁₂H₈ClN₃O₃
• Molecular Weight: 277.66322
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Tyrosine Kinase Inhibitors
• Mol File: 214476-09-2.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 485.3°C at 760 mmHg
• Flash Point: 247.3°C
• Appearance: /
• Density: 1.47g/cm³
• Vapor Pressure: 1.43E-09mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO
• PKA: -1.04±0.41(Predicted)
• CAS DataBase Reference: 4-Chloro-3-cyano-7-ethoxy-6-nitroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-3-cyano-7-ethoxy-6-nitroquinoline(214476-09-2)
• EPA Substance Registry System: 4-Chloro-3-cyano-7-ethoxy-6-nitroquinoline(214476-09-2)

Safety Data

• Hazardous Substances Data: 214476-09-2(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

4-Chloro-3-cyano-7-ethoxy-6-nitroquinoline can be used in the preparation of tyrosine kinase inhibiting antitumor agents.

InChI:InChI=1/C12H8ClN3O3/c1-2-19-11-4-9-8(3-10(11)16(17)18)12(13)7(5-14)6-15-9/h3-4,6H,2H2,1H3

Upstream product

• 10026-13-8 phosphorus pentachloride 
• 214476-08-1 7-Ethoxy-4-hydroxy-6-nitro-quinoline-3-carbonitrile 
• 2369-13-3 3-fluoro-4-nitroaniline 
• 848133-75-5 3-cyano-4-hydroxyl-6-acetamido-7-ethoxyquinoline 
• 621-33-0 m-phenetidine 
• 361162-91-6 5-ethoxy-2-methyl-4-nitroacetanilide 
• 214476-07-0 7-ethoxy-4-hydroxyquinoline-3-carbonitrile 
• 361162-90-5 5-methoxy-2-methyl-4-nitroacetanilide 
• 116435-75-7 3-(ethyloxy)-4-nitroaniline 
• 106579-00-4 5-methoxy-2-methyl-4-nitroaniline 
• 909513-02-6 (E)-2-Cyano-3-(3-ethoxy-phenylamino)-acrylic acid ethyl ester 
• 492456-51-6 (E)-2-Cyano-3-(3-ethoxy-4-nitro-phenylamino)-acrylic acid ethyl ester 
• 361162-92-7 2-acetylamino-4-ethoxy-5-nitrobenzoic acid 

Downstream Products

• 214485-68-4 4-(3-Bromo-phenylamino)-7-ethoxy-6-nitro-quinoline-3-carbonitrile 
• 263171-30-8 4-[3-chloro-4-(1H-imidazol-1-ylmethyl) anilino]-7-ethoxy-6-nitro-3-quinolinecarbonitrile 
• 263171-08-0 4-[3-chloro-4-(4-pyridinyloxy)anilino]-7-ethoxy-6-nitro-3-quinolinecarbonitrile 
• 848133-87-9 6-amino-4-chloro-7-ethoxyquinoline-3-carbonitrile 
• 214485-69-5 6-amino-4-(3-bromo-phenylamino)-7-ethoxy-quinoline-3-carbonitrile 
• 361162-95-0 6-amino-4-(3-chloro-4-fluoro-phenylamino)-7-ethoxy-quinoline-3-carbonitrile 
• 492456-86-7 N-[4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxy-6-quinolinyl]-2-butenamide 
• 257933-82-7 pelitinib 

Relevant articles and documents

NITROGENOUS HETEROCYCLIC COMPOUND, PREPARATION METHOD, INTERMEDIATE, COMPOSITION, AND APPLICATION

A nitrogenous heterocyclic compound, a preparation method, an intermediate, a composition, and an application. The present invention provides a nitrogenous heterocyclic compound as represented by formula I, pharmaceutically acceptable salts thereof, enantiomers thereof, diastereoisomers thereof, tautomers thereof, solvates thereof, metabolites thereof, or prodrugs thereof. The compound has high inhibitory activity against ErbB2 tyrosine kinase, has good inhibitory activity against human breast cancer cells BT-474, human gastric cancer cells NCI-N87 and the like with high expression of ErbB2, and in addition has relatively weak inhibitory activity against EGFR kinase, that is, the compound is an EGFR/ErbB2 double target inhibitor that attenuates EGFR kinase inhibitory activity or a small-molecule inhibitor having selectivity for an ErbB2 target. (I)

A method of synthesizing a neratinib intermediate, 3-cyano-4-chloro-6-amino-7-ethoxyquinoline

A method of synthesizing a neratinib intermediate that is 3-cyano-4-chloro-6-amino-7-ethoxyquinoline is disclosed. The method includes (1) subjecting methyl 4-ethoxy-2-chloro-5-nitrobenzoate and 3-amino acrylonitrile to a condensation reaction under the action of a catalyst 1 to obtain 2-(4-ethoxy-2-chloro-5-nitrobenzoyl)-3-amino acrylonitrile; (2) subjecting the 2-(4-ethoxy-2-chloro-5-nitrobenzoyl)-3-amino acrylonitrile to a cyclization reaction to obtain 3-cyano-4-oxo-6-nitro-7-ethoxy-1,4-dihydroquinoline; (3) subjecting the 3-cyano-4-oxo-6-nitro-7-ethoxy-1,4-dihydroquinoline and phosphorus oxychloride to a chlorination reaction to obtain 3-cyano-4-chloro-6-nitro-7-ethoxyquinoline; and (4) subjecting the 3-cyano-4-chloro-6-nitro-7-ethoxyquinoline and hydrazine hydrate to a reduction reaction under the action of a catalyst 2 to obtain a target product. According to the method, synthetic steps are few, reaction conditions are mild, agents are cheap and easily available, operation is simple and the total yield is high. The method provides a novel route for preparation of neratinib and the intermediate.

USE OF CYANOQUINOLINES FOR TREATING OR INHIBITING COLONIC POLYPS

This invention provides a method of treating or inhibiting colonic polyps which comprises providing a compound of formula (1); wherein R1, R2, R3, R4, X, Y, and n are defined hereinbefore, or a pharmaceutically acceptable salt thereof.