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Method for synthesizing 2-methyl-3-nitrophenylacetic acid

A technology of methylphenylacetic acid and nitrophenylacetic acid, which is applied in the preparation of nitro compounds, organic chemistry, etc., can solve the problems of unspecified purity and achieve the effect of low price and few reaction steps

Inactive Publication Date: 2012-10-10
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In this method, 2-methyl-3-nitrophenylacetic acid is obtained as a colorless oily substance through two reaction steps, and the purity of the obtained 2-methyl-3-nitrophenylacetic acid is not specified.

Method used

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  • Method for synthesizing 2-methyl-3-nitrophenylacetic acid
  • Method for synthesizing 2-methyl-3-nitrophenylacetic acid
  • Method for synthesizing 2-methyl-3-nitrophenylacetic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] In a reaction flask equipped with a thermometer and a stirring device, add 20g (0.133moL) of 2-methylphenylacetic acid, 15g (0.147moL) of acetic anhydride and 20mL of dichloromethane respectively, stir and cool down until the reaction temperature is 0°C, and start Add 12g (0.190moL) of 98% concentrated nitric acid dropwise. After the dropwise addition, continue the reaction at a reaction temperature of 0°C to 5°C for 3.0h, then filter to obtain 15.76g of 2-methyl-3-nitrophenylacetic acid. The rate is 60.6%.

[0026] Structure Identification:

[0027] IR (potassium bromide compressed tablet, cm -1 ): 1718 and 1267 (COOH), 1526 and 1340 (NO 2 ).

[0028] H'NMR (500MHz, DMSO): δ2.28(3H, s), 3.79(2H, s), 7.37~7.40(1H, t), 7.54~7.55(1H, d), 7.73~7.74(1H, d ), 12.56 (1H, s).

[0029] Elemental analysis, molecular formula C 9 h 9 NO 4 ,

[0030] Theoretical value (%): C 55.38, H 4.58, N 7.23.

[0031] Found value (%): C 55.39, H 4.65, N 7.18.

[0032] MS (m / z): 195 ...

Embodiment 2

[0035] In a reaction flask equipped with a thermometer and a stirring device, add 20g (0.133moL) of 2-methylphenylacetic acid, 15g (0.147moL) of acetic anhydride and 20mL of dichloromethane respectively, stir and cool down until the reaction temperature is 0°C, and start 13.4g (0.212moL) of 98% concentrated nitric acid was added dropwise. After the dropwise addition, the reaction was continued at a reaction temperature of 0°C to 5°C for 2.0h, and then filtered to obtain 15.96g of 2-methyl-3-nitrophenylacetic acid. The yield was 61.4%.

[0036] Structure Identification:

[0037] IR (potassium bromide compressed tablet, cm -1 ): 1718 and 1263 (COOH), 1524 and 1333 (NO 2 ).

[0038] H'NMR (500MHz, DMSO): δ2.43(3H, s), 3.79(2H, s), 7.26~7.32(1H, t), 7.43~7.44(1H, d), 7.71~7.73(1H, d ), 12.54 (1H, s).

[0039] Elemental analysis, molecular formula C 9 h 9 NO 4 ,

[0040] Theoretical value (%): C 55.38, H 4.58, N 7.23.

[0041] Found value (%): C 55.42, H 4.65, N 7.14.

...

Embodiment 3

[0045] In a reaction flask equipped with a thermometer and a stirring device, add 20g (0.133moL) of 2-methylphenylacetic acid, 15g (0.147moL) of acetic anhydride and 20mL of dichloromethane respectively, stir and cool down until the reaction temperature is 0°C, and start Add 12.9 g (0.205 moL) of 98% concentrated nitric acid dropwise. After the dropwise addition, continue the reaction at 5-10° C. for 1.0 h, then filter to obtain 15.50 g of 2-methyl-3-nitrophenylacetic acid. The yield is 59.6%.

[0046] Structure Identification:

[0047] IR (potassium bromide compressed tablet, cm -1 ): 1718 and 1264 (COOH), 1525 and 1334 (NO 2 ).

[0048] H'NMR (500MHz, DMSO): δ2.33(3H, s), 3.78(2H, s), 7.26~7.33(1H, t), 7.43~7.44(1H, d), 7.71~7.73(1H, d ), 12.52 (1H, s).

[0049] Elemental analysis, molecular formula C 9 h 9 NO 4 ,

[0050] Theoretical value (%): C 55.38, H 4.58, N 7.23.

[0051]Found value (%): C 55.70, H 4.80, N 7.10.

[0052] MS (m / z): 195

[0053] The above an...

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Abstract

The invention discloses a synthesis method of 2-methyl-3-nitrophenylacetic acid. The method comprises the following steps: 2-methylphenylacetic acid is taken as a raw material; 2-methylphenylacetic acid, acetic anhydride and dichloromethane are respectively added to a reaction bottle, stirred, cooled to be 0 DEG C and added with 98% nitric acid in a dripping manner; reaction temperature is between -10 DEG C and 10 DEG C and reaction is carried out for 1h to 3h; filtering is carried out; a target product (I) is obtained, wherein, the mole ratio of 2-methylphenylacetic acid, nitric acid and acetic anhydride is 1:1.40 to 1.60:1.10. The method is mainly applied to the synthesis of 2-methyl-3-nitrophenylacetic acid compounds.

Description

Technical field: [0001] The invention relates to a method for synthesizing 2-methyl-3-nitrophenylacetic acid, which belongs to organic synthesis. Background technique: [0002] 2-Methyl-3-nitrophenylacetic acid is a light yellow to white solid powder with a melting point of 131°C to 134°C, soluble in water and alcohol, and is an important intermediate for the synthesis of ropinirole hydrochloride. Ropinirole hydrochloride is a newly developed second-generation dopamine receptor agonist for the treatment of Parkinson's disease (PD). It has a simple chemical structure very similar to natural dopamine, and has very few neurological side effects. [0003] V.Askam and R.H.L.Deeks.Oxidation and Claisen Condensation Products of3-Nitro-0-xylene[J]J.Chem.Soc.(C), 1969:1935~1936 reported a kind of o-xylene as raw material, after nitration , oxidation, hydrolysis, reduction, chlorination, cyanide, hydrolysis and other seven-step reaction steps, the method for synthesizing 2-methyl-3-n...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C205/56C07C201/08
Inventor 张丽洁惠培华樊学忠姬明理崔军民黄小梧苏天铎柳恒姚逸伦
Owner XIAN MODERN CHEM RES INST
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