2-Oxo-2,3-Dihydro-1H-indole-6-carboxylic acid methyl ester
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2-Oxo-2,3-Dihydro-1H-indole-6-carboxylic acid methyl ester
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CAS No:
14192-26-8
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Formula:
C10H9NO3
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Chemical Name:
2-Oxo-2,3-Dihydro-1H-indole-6-carboxylic acid methyl ester
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Synonyms:
1H-Indole-6-carboxylic acid,2,3-dihydro-2-oxo-,methyl ester;6-Indolinecarboxylic acid,2-oxo-,methyl ester;6-(Methoxycarbonyl)-2-indolone;Methyl 2-oxoindoline-6-carboxylate;2-Oxo-2,3-Dihydro-1H-indole-6-carboxylic acid methyl ester;Methyl 2-oxindole-6-carboxylate
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CAS No:
2-Oxo-2,3-Dihydro-1H-indole-6-carboxylic acid methyl ester Basic Attributes
191.19
191.18
604-263-8
2933790090
Characteristics
55.4
0.6
1.3±0.1 g/cm3
184-190°C
388.1°C at 760 mmHg
188.5±27.9 °C
1.573
3.15E-06mmHg at 25°C
2-Oxo-2,3-Dihydro-1H-indole-6-carboxylic acid methyl ester Use and Manufacturing
48.3 g of methyl 4-methoxycarbonylmethyl-3-nitro-benzoate are dissolved in 800 ml of concentrated acetic acid, 5.0 g of palladium on carbon (10percent) are added and the solution is hydrogenated for 2.5 hours at room temperature and 50 psi. The catalyst is filtered off and the filtrate is evaporated down. The residue is taken up in 150 ml of tert.-butylmethyl ether, filtered again and dried in vacuo at 100° C. [01142] Yield: 28.6 g (98percent of theory), R4-Methoxycarbonylmethyl-3-nitrobenzoic acid methyl ester (4.2 g, 16.6 mmol) was dissolved in acetic acid (90 ml) and hydrogenated (50 psi) at room temperature for 2.5 hours using 0.6 g 10percent palladium on charcoal as catalyst. 45 ° C and at40-50psi, 1.3 kg of [4- (methoxycarbonyl) -2-nitrophenyl] -malonic acid dimethyl ester was dissolved in 9 L of acetic acid solution, Add 0.13 kg of 10percent K2CO3 solution to hydrogenate. After completion of hydrogenation, The hydrogenated product was heated to 115 ° C and the reaction was continued for 2 h. The catalyst was filtered off hot, And 18 L of water was added at about 50 ° C. The product was cooled to 5 ° C, centrifuged, dried at 50 ° C, The yield was 87.2percent and the purity was 99.8percent.2-carbonylindolone-6-carboxylic acid (40 g, 0.23 mol) was added to the reaction flask, 200 ml of methanol was added, and the mixture was slowly added dropwise, and the temperature was raised to 60 ° C by slowly dropping thionyl chloride (32 g, 0.27 mol). The reaction was carried out for 6 hours. After completion of the reaction, the reaction mixture was evaporated to dryness, ground with methanol, filtered and dried to obtain 40 g of 2-carbonylindolone-6-carboxylate in a yield of 93percent.The following compound is prepared analogously to Example V:A mixture of compound VI (lOg) and acetic anhydride (40ml) was stirred at about 110C-120C for about 2h. To this reaction mass, triethyl orthobenzoate (35.18gm) was slowly added at about 115-125C for 3h and distilled out low boiler simultaneously at about 120-125C. Then the reaction mass was cooled to about 90C, and concentrated under vacuum to obtain crude compound of formula V.
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2-Oxo-2,3-Dihydro-1H-indole-6-carboxylic acid methyl ester
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