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Compounds of '3-(5-sustituted oxy-2,4-dinitro-phenyl)-2-oxo-propionic acid ester', process and applications thereof

A compound and alkynyl technology, applied in the preparation of nitro compounds, organic chemistry, etc., can solve problems such as tedious work process

Inactive Publication Date: 2016-04-06
ANTHEM BIOSCI PVT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this synthetic method involves many steps and the isolation of higher intermediates further involves a tedious work process

Method used

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  • Compounds of '3-(5-sustituted oxy-2,4-dinitro-phenyl)-2-oxo-propionic acid ester', process and applications thereof
  • Compounds of '3-(5-sustituted oxy-2,4-dinitro-phenyl)-2-oxo-propionic acid ester', process and applications thereof
  • Compounds of '3-(5-sustituted oxy-2,4-dinitro-phenyl)-2-oxo-propionic acid ester', process and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0185] Example 1: Preparation of 1-fluoro-5-methyl-2,4-dinitro-benzene [formula III, wherein R3 is F]

[0186]

[0187] 67% nitric acid (approximately 250 mL, 5.6 moles) was charged at a temperature of approximately 25-30 °C to a three-neck round bottom flask equipped with a mechanical stirrer. Thereafter concentrated sulfuric acid (about 360 mL, 6.75 mol) was added dropwise at about 0°C over a period of about 30 minutes. 1-Fluoro-3-methyl-benzene [formula II, wherein R3 is F] (about 100 mL, 0.9 mol) was added dropwise to the obtained Nitrate mixture.

[0188] The reaction mixture obtained was stirred at a temperature in the range of about 20-25° C. during about 30 minutes. The completion of the reaction was monitored by thin layer chromatography (TLC) (10% ethyl acetate in petroleum ether as solvent system). After this time, the reaction mixture was poured onto crushed ice (about 3.0 L) to precipitate the product. The precipitated product was filtered and dried under...

Embodiment 2A

[0192] Example 2A: 3-(5-methoxy-2,4-dinitro-phenyl)-2-oxo-propionic acid methyl ester [formula I, wherein, R1 is-CH 3 and R2 is -CH 3 ] preparation

[0193]

[0194] To a suspension of 1-fluoro-5-methyl-2,4-dinitro-benzene (ca. about 108 g, 1.9 moles) and diethyl oxalate (136 mL, 1.0 moles). The obtained orange suspension was brought slowly to a temperature of about 15-20° C. in about 2 hours and stirred continuously at a temperature of about 15-20° C. during a period of about 16 hours. The reaction mixture was quenched with 1.5N HCl (about 200 mL), and the resulting precipitated solid was filtered and dried under house vacuum to obtain the product [3-(5-methoxy-2,4-dinitro- Phenyl)-2-oxo-propionic acid methyl ester] (ca. 125 g, 85%).

[0195] 1 HNMR (CDCl 3 , 300MHz): 3.98(s, 3H), 4.11(s, 3H), 4.65(s, 2H), 7.00(s, 1H), 8.84(s, 1H);

[0196] LC-MS (ESI): 297.0 (M-H);

[0197] HPLC purity: 99.12%

[0198] Melting range: 142.7°C-143.2°C

[0199] IR (KBr,...

Embodiment 2B

[0220] Example 2B: Methyl 3-(5-methoxy-2,4-dinitro-phenyl)-2-oxo-propionate [sodium salt of formula I, which where R1 is -CH 3 and R2 is -CH 3 ] preparation

[0221]

[0222] Sodium salt of formula I

[0223] To a suspension of 1-fluoro-5-methyl-2,4-dinitro-benzene (ca. 4.0 g, 16.0 mmol) in methanol (ca. 50 mL) was added sodium methoxide at a temperature of about 0 °C (about 4.3g, 76mmol) and diethyl oxalate (about 5.4mL, 37mmol). The obtained orange suspension was slowly brought to a temperature of about 15-20° C. within 2 hours and stirred continuously at a temperature of about 15-20° C. during a period of about 16 hours. The completion of the reaction was monitored by TLC. The obtained precipitated solid was filtered and dried under house vacuum to obtain the product sodium [2-hydroxy-3-(5-methoxy-2,4-dinitro-phenyl)-methylacrylate as a brown solid salt] (about 5.0 g, 86%).

[0224] 1 HNMR (DMSO-d 6 ,400MHz): 3.66(s, 3H), 3.87(s, 3H), 6.87(s, 1H), 8.6...

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Abstract

The present disclosure relates to compounds of Formula (I) and process of obtaining the same. Said compounds of Formula (I) is employed in the syntheses of pyrroloquinoline quinone (PQQ), 4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid 2-allyl ester, 5-ethoxy-5-hydroxy-4-oxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid, 5-hydroxy-6-(1,1,4-trioxo-1 lambda*6*-1,2,5-thiadiazolidin-2-yl)-1H-indole-2-carboxylic acid and its pharmaceutically acceptable salts. Said syntheses of compounds via compounds of Formula (I) as intermediates employ minimum number of steps resulting in a shorter process and has improved efficiency along with many other advantages.

Description

technical field [0001] The present disclosure relates to compounds of formula 1 and methods of obtaining them. Said compounds of formula I have various applications, more particularly in the synthesis of pyrroloquinoline quinone (PQQ), 4,5-dioxo-4,5-dihydro-1H-pyrrole[2 ,3-f]quinoline-2,7,9-tricarboxylic acid 2-allyl ester, 5-ethoxy-5-hydroxyl-4-oxyl-4,5-dihydro-1H-pyrrole[2 ,3-f]quinoline-2,7,9-tricarboxylic acid, 5-hydroxy-6-(1,1,4-trioxy-1λ*6*-1,2,5-thiazolidine-2- Base)-1H-indole-2-carboxylic acid (5-hydroxy-6-(1,1,4-trioxo-1lambda*6*-1,2,5-thiadiazolidin-2-yl)-1H-indole- 2-carboxylic acid) and pharmaceutically acceptable salts thereof. [0002] In addition, the synthesis of PQQ and its salts is carried out via the compound of formula I represented below as an intermediate: [0003] [0004] Wherein, R1 and R2 are independently selected from the group comprising: hydrogen, straight chain or branched chain C 1-8 Alkyl, straight chain or branched C 1-8 Alkenyl, stra...

Claims

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Application Information

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IPC IPC(8): C07C205/12C07C205/56C07D471/04
CPCC07C201/08C07C205/56C07D471/04C07C205/12
Inventor 拉朱卢·加瓦拉 戈文达加内什·萨姆巴西瓦姆汤姆·托马斯·皮蒂亚帕拉姆皮尔拉温德拉·钱德拉帕 科拉曼加拉
Owner ANTHEM BIOSCI PVT
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