ChemicalBook CAS DataBase List 1-METHYL-3-PHENYL-1H-PYRAZOLE-5-CARBOXYLIC ACID

1-METHYL-3-PHENYL-1H-PYRAZOLE-5-CARBOXYLIC ACID synthesis

7synthesis methods

Product Name:1-METHYL-3-PHENYL-1H-PYRAZOLE-5-CARBOXYLIC ACID
CAS Number:10250-64-3
Molecular formula:C11H10N2O2
Molecular Weight:202.21

1-Methyl-3-phenylpyrazol-5-carbonsaeure-methylester

10250-62-1

10250-64-3

The general procedure for the synthesis of 1-methyl-3-phenyl-1H-pyrazole-5-carboxylic acid from methyl 1-methyl-3-phenyl-1H-pyrazole-5-carboxylate was as follows: 1-methyl-3-phenyl-1H-pyrazole-5-carboxylic acid methyl ester (1.00 g, 6.23 mmol) was dissolved in a mixed solvent of ethanol (10 mL) and water (10 mL), and then lithium hydroxide mono hydrate (0.582 g, 13.87 mmol). The reaction mixture was stirred at 50 °C until the reaction was complete as monitored by high performance liquid chromatography (HPLC). After completion of the reaction, the mixture was concentrated to dryness and the residue was dissolved in water and extracted with dichloromethane (DCM). The aqueous phase was acidified with 1N hydrochloric acid to pH < 3. The precipitated solid was collected by filtration and dried under high vacuum to afford 1-methyl-3-phenyl-1H-pyrazole-5-carboxylic acid (0.887 g, 95% yield) as a white solid. The mass spectrum (APCI positive ion mode) showed m/z 203 (100%) ([M+H]+).

ETHYL 1-METHYL-3-PHENYL-1H-PYRAZOLE-5-CARBOXYLATE

10250-63-2
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$49.00/1g

10250-64-3
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$21.00/100mg

Yield: 93.1%

Reaction Conditions:

with sodium hydroxide in methanol at 20; for 2 h;

Steps:

8.2 Step2: Preparation of Compound 1-3
To a solution of 1-2 (247.5 mg, 1.1 mmol) in MeOH (5 mL) was added sodium hydroxide solution (10 mL, 4 M). The reaction mixture was stirred at room temperature for 2 hours and concentrated under reduced pressure to remove MeOH. The aqueous phase was acidified with aqueous HCl (1 M) till pH=3 and the mixture was extracted with EtOAc, dried with anhydrous Na₂SO₄, filtered and concentrated to give the crude product. The crude product was purified by silica gel chromatography eluted to give product 1-3 (207.0 mg, 93.1%). MS m/z [ESI]: 203.1 [M+1].

References:

SUZHOU SINOVENT PHARMACEUTICALS CO., LTD.;WANG, Yonghui;ZHU, Yan;ZHOU, Juan;GAO, Yujun;WANG, Shiqun;WANG, Dong;LIU, Wandeng;SHEN, Ximing;HONG, Binbin;LIU, Tao;WU, Yaodong;LI, Chunqi US2018/271846, 2018, A1 Location in patent:Paragraph 0176; 0180; 0181

10250-62-1
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10250-64-3
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$21.00/100mg

References

98-86-2 Synthesis