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ChemicalBook CAS DataBase List Chlorantraniliprole
500008-45-7

Chlorantraniliprole synthesis

13synthesis methods
Chlorantraniliprole was synthesized by reaction of 3-bromo-1-(3-chloropyridin-2-pyridinyl)-1H-pyrazole-5carboxylic acid with 2-amino-5-chloro-3-methylbenzoic acid.3-bromo-1-(3-chloropyridin-2-pyridinyl)-1H-pyrazole5-carboxylic acid was prepared by reaction of maleic anhydride with 2,3-dichloropyridine as starting materials in eight steps.2-Amino-5-chloro-3-methylbenzoic acid was prepared by reaction of 2-amino-3-methylbenzoic acid in one step.The structure of target compound was conf irmed by 1H NMR.Total yield was 36.3%(calculated with 2,3-dichloropyridine),and purity determined by HPLC was over 95%.
500011-86-9 Synthesis
3-BroMo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid

500011-86-9
169 suppliers
$8.00/250mg

890707-28-5 Synthesis
Bardoxolone

890707-28-5
163 suppliers
$5.00/100mg

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Yield:500008-45-7 97%

Reaction Conditions:

with 3-Methylpyridine;methanesulfonyl chloride in propiononitrile at -5 - 20; for 4 h;Product distribution / selectivity;

Steps:

13
EXAMPLE 13 Preparation of 3 -bromo-iV- [4-chloro-2-methyl-6- [(methylamino)carbonyl]phenyl] - l-(3-chloro-2-pyridinyl)-lH-pyrazole-5-carboxamide in propionitrileTo a mixture of 3-bromo-l-(3-chloro-2-pyridinyl)-lH-pyrazole-5-carboxylic acid (see PCT Patent Publication WO 03/015519 for preparation) (6.05 g, 20.0 mmol) and 2-amino-5-chloro-N,3-dimethylbenzamide (i.e. the product of Examples 1, 3, 4 and 5) (4.17 g,21.0 mmol) in propionitrile (18 mL) was added 3-picoline (5.06 mL, 4.84 g, 52 mmol). The mixture was cooled to -5 °C, and then methanesulfonyl chloride (1.86 mL, 2.75 g, 24 mmol) was added dropwise at -5 to 0 °C. The mixture was stirred for 1 h at 0 to 5 °C, and then for 3 h at room temperature. Then water (9 mL) was added dropwise and the mixture was stirred at room temperature for 1 h. The mixture was filtered, and the solids were washed with 3:1 propionitrile-water (2 x 4 mL), then with propionitrile (2 x 4 mL), and dried under nitrogen to afford the title compound as a nearly white powder, 9.37 g (97.0% uncorrected yield).

References:

E.I. DUPONT DE NEMOURS AND COMPANY WO2006/62978, 2006, A1 Location in patent:Page/Page column 28

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