ChemicalBook CAS DataBase List 1,4-Dihydro-2,6-dimethyl-4-(2',3'-dichlorophenyl)-5-carboxy methyl-3-pyridinecarboxylic acid

1,4-Dihydro-2,6-dimethyl-4-(2',3'-dichlorophenyl)-5-carboxy methyl-3-pyridinecarboxylic acid synthesis

6synthesis methods

Product Name:1,4-Dihydro-2,6-dimethyl-4-(2',3'-dichlorophenyl)-5-carboxy methyl-3-pyridinecarboxylic acid
CAS Number:123853-39-4
Molecular formula:C16H15Cl2NO4
Molecular Weight:356.2

4-(2,3-Dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-cyano-ethyl) ester 5-methyl ester

110962-94-2

1,4-Dihydro-2,6-dimethyl-4-(2',3'-dichlorophenyl)-5-carboxy methyl-3-pyridinecarboxylic acid

123853-39-4

The general procedure for the synthesis of 4-(2,3-dichlorophenyl)-5-(methoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid, using 3-(2-cyanoethyl) 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3-dicarboxylate as a starting material, was as follows: in a three-necked flask equipped with a stirrer, add 400 g of Intermediate II and 2 L of isopropanol and stirred until completely dissolved. Subsequently, 30 g of potassium hydroxide and 10 g of triethylbenzyl ammonium bromide were added, heated to 80 °C and stirred at reflux for 5 to 6 hours. After completion of the reaction, it was cooled to room temperature and the reaction mixture was filtered. The filtrate was concentrated to dryness under reduced pressure. To the dried residue, 2 L of dichloromethane and 2 L of water were added, stirred for 10 minutes and left to stratify. Dilute hydrochloric acid was slowly added dropwise to the aqueous phase under ice bath conditions to adjust the pH to 4.5 and stirring was continued for 1 hour. Subsequently, filtration was carried out and the filter cake was washed with pure water to pH=7. After drying, 260 g of product was obtained and the purity was 96.11% by HPLC. In another reaction flask, 130 g of crude intermediate butyl clovedipine and 650 ml of ethyl acetate were added, stirred and heated to 40 °C, maintained for 10 min and then hot filtered. The filter cake was dried to give 122 g of pale yellow solid, the important intermediate clovidipine butyrate. The purity was 99.09% and the yield was 93% by HPLC. The total yield of the present synthesis method was 53%, which gave an important intermediate of clovidipine butyrate acid with high purity.

91189-59-2 Synthesis

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Yield: 99%

Reaction Conditions:

with methanesulfonic acid at 80; for 3 h;Temperature;

Steps:

1-5 Preparation of 4-(-2,3-dichlorophenyl) -1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-3-pyridinecarboxylic acid (I), its reaction formula as follows:
4-(-2,3-dichlorophenyl) -1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid methyl ester (II)(500g, 1.35mol) was added to methanesulfonic acid (1000g),Heat to the reaction temperature of 80 ° C with stirring,And stirred at this temperature for 3h,The reaction temperature is reduced to 5-10 ° C, filtered, and the filter cake is washed with a small amount of cold methanesulfonic acid.Drying to obtain 476.2g of product (I),Yield: 99%.

References:

Shanghai Institute of Technology;Fang Yahui;Yao Lingyan CN110615757, 2019, A Location in patent:Paragraph 0040-0052

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123853-39-4
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References