ChemicalBook CAS DataBase List ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID

ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID synthesis

7synthesis methods

Product Name:ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID
CAS Number:31842-01-0
Molecular formula:C17H15NO3
Molecular Weight:281.31

Benzeneacetic acid, 4-(1,3-dihydro-1-oxo-2H-isoindol-2-yl)-α-methyl-, ethyl ester

36691-00-6
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ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID

31842-01-0
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$35.70/1g

Yield:31842-01-0 83%

Reaction Conditions:

with potassium hydroxide in ethanol for 3 h;Reflux;

Steps:

Preparation of rac-Indoprofen (39) from 38
To a solution of ester (38; 100 mg, 0.32 mmol) in EtOH (19 mL) was added 10% KOH (1 mL), and the mixture was heated at reflux for 3 h. After cooled to room temperature, the reaction mixture was evaporated in vacuo, and the residue was dissolved in cold water (10 mL). Acidification of aqueous solution gave precipitates, which were collected by filtration. Since the crude material was very hygroscopic, it was immediately recrystallized from EtOH to give the analytically pure sample of rac-indoprofen [39; 78 mg, 83%, mp 205-207 oC (lit.,10 213-214 oC); pure from 1H NMR spectra] as slightly yellow crystalline solids.The result of combustion analyses proved that our sample was hydrated: Anal. Calcd forC17H15NO3+1/3H2O: C, 71.07; H, 5.50; N, 4.87. Found: C, 71.01; H, 5.44; N, 4.63.

References:

Takahashi, Ichiro;Kawakami, Teruki;Hirano, Etsushi;Kimino, Mako;Kamimura, Shigeki;Miwa, Takayuki;Tamura, Takanori;Tazaki, Ryo;Kitajima, Hidehiko;Hatanaka, Minoru;Isa, Kimio;Hosoi, Shinzo [Heterocycles,2016,vol. 93,# 2,p. 557 - 571]

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