141761-83-3

Basic information

• Product Name: 6-Chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid methyl ester
• Synonyms: 6-Chloro-3,4-Dihydro-4-Methyl-3-Oxo-2H-1,4-Benzoxazine-8-CarboxylicAcidMethlyEster;6-Chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid methyl ester;2H-1,4-Benzoxazine-8-carboxylicacid,6-chloro-3,4-dihydro-4-Methyl-3-oxo-, Methyl ester;Methyl 6-chloro-4-Methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylate;methyl 6-chloro-4-methyl-3-oxo-1,4-benzoxazine-8-carboxylate;2H-1,4-Benzoxazine-8-carboxylic
• CAS NO: 141761-83-3
• Molecular Formula: C₁₁H₁₀ClNO₄
• Molecular Weight: 255.65
• EINECS: 1533716-785-6
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 141761-83-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 498.8 °C at 760 mmHg
• Flash Point: 255.5 °C
• Appearance: /
• Density: 1.384
• Vapor Pressure: 4.4E-10mmHg at 25°C
• Refractive Index: 1.568
• Storage Temp.: 2-8°C
• PKA: -1.00±0.20(Predicted)
• CAS DataBase Reference: 6-Chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid methyl ester(141761-83-3)
• EPA Substance Registry System: 6-Chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid methyl ester(141761-83-3)

Safety Data

• Hazardous Substances Data: 141761-83-3(Hazardous Substances Data)

Usage

Uses

Azasetron intermediate.

InChI:InChI=1/C11H10ClNO4/c1-13-8-4-6(12)3-7(11(15)16-2)10(8)17-5-9(13)14/h3-4H,5H2,1-2H3

Upstream product

• 4068-78-4 methyl 5-chloro-2-hydroxybenzoate 
• 5043-81-2 3-amino-5-chloro-2-hydroxybenzoic acid methyl ester 
• 79-04-9 chloroacetyl chloride 
• 616-38-6 carbonic acid dimethyl ester 
• 123040-75-5 methyl 6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylate 
• 74-88-4 methyl iodide 
• 5043-79-8 5-chloro-2-hydroxy-3-nitrobenzoic acid methyl ester 

Downstream Products

• 123040-16-4 Azasetron hydrochloride 
• 141762-06-3 6-Chloro-4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid (1-benzyl-piperidin-4-yl)-amide 
• 141762-05-2 6-Chloro-4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid (1-benzyl-piperidin-3-yl)-amide 
• 123040-69-7 azasetron 
• 123040-50-6 6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid chloride 
• 123040-79-9 6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid 

Relevant articles and documents

Hydrochloric acid stabilizing method for synthesizing intermediate (by machine translation)

The invention relates to preparation of an azasetron hydrochloride intermediate and especially relates to an intermediate methyl 6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazinyl-8-carboxylate synthesis method. The synthesis method comprises that methyl 6-chloro-3-oxo-3,4-dihydro-2H-1,4-benzoxazinyl-8-carboxylate and methyl iodide undergo a methylation reaction, wherein in the reaction process, water is used and promotes the forward reaction and the reaction product is treated to form a final product. The synthesis method solves the problem that the prior art has incomplete methylation reaction and long reaction time. The product obtained by the synthesis method has stable substance content and high purity. The synthesis method improves production efficiency and is suitable for industrial production.

Synthesis and pharmacology of 3,4-dihydro-3-oxo-1,4-benzoxazine-8-carboxamide derivatives, a new class of potent serotonin-3 (5-HT3) receptor antagonists

A series of 3,4-dihydro-3-oxo-1,4-benzoxazine-8-carboxamide derivatives was synthesized and evaluated for serotonin-3 (5-HT3) receptor antagonistic activity assessed by their ability to antagonize the von Bezold-Jarish (BJ) effect in rats. Derivatives bearing 1-azabicyclo[2.2.2]oct-3-yl moiety as a basic function attached to the carboxamide at position 8 showed more potent antagonistic activity than those bearing the other three basic moieties. Structure activity relationships of this series showed that methyl and chloro groups were more effective as substituents at positions 4 and 6, respectively. The representative compound 15 (Y-25130) in this series showed potent antagonistic activity on the BJ effect (ED50 = 1.3 μg/kg i.v.), high affinity for 5-HT3 receptor (K(i) = 2.9 nM) and complete protection against cisplatin-induced emesis in dogs at a dose of 0.1 mg/kg i.v.