| Identification | More | [Name]
Methyl 2-oxoindole-6-carboxylate | [CAS]
14192-26-8 | [Synonyms]
2-INDOLINONE-6-METHYLCARBOXYLATE
2-OXO-2,3-DIHYDRO-1H-INDOLE-6-CARBOXYLIC ACID METHYL ESTER
2-OXO-6-INDOLINECARBOXYLIC ACID METHYL ESTER
6-METHOXYCARBONYL-2-OXINDOLE
METHYL 2-OXINDOLINE-6-CARBOXYLATE
METHYL 2-OXOINDOLINE-6-CARBOXYLATE
METHYL OXINDOLE-6-CARBOXYLATE
OXINDOLE-6-CARBOXYLIC ACID METHYL ESTER
2-Oxindole-6-carboxylic acid methyl ester
Methyl 2-oxoindoline-6-carboxylate 97%
Methyl-2-Dxoindline-6-carboxylate
Methyl 2-oxoindole-6-carboxylate | [EINECS(EC#)]
1308068-626-2 | [Molecular Formula]
C10H7NO3 | [MDL Number]
MFCD03095196 | [Molecular Weight]
189.17 | [MOL File]
14192-26-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
184-190°C | [Boiling point ]
388.1±42.0 °C(Predicted) | [density ]
1.283±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
13.50±0.20(Predicted) | [color ]
White to Off-White | [InChI]
InChI=1S/C10H9NO3/c1-14-10(13)7-3-2-6-5-9(12)11-8(6)4-7/h2-4H,5H2,1H3,(H,11,12) | [InChIKey]
YFTGUNWFFVDLNM-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=CC(C(OC)=O)=C2)CC1=O | [CAS DataBase Reference]
14192-26-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [Hazard Note ]
Irritant | [HS Code ]
2933790090 |
| Hazard Information | Back Directory | [Uses]
Methyl Oxindole-6-carboxylate is an intermediate used to prepare BIBF 1120, an indolinone as triple angiokinase inhibitors. | [Synthesis]
General procedure for the synthesis of methyl 2-oxoindoline-6-carboxylate from methyl 4-(2-methoxy-2-oxoethyl)-3-nitrobenzoate: 48.3 g of methyl 4-(2-methoxy-2-oxoethyl)-3-nitrobenzoate was dissolved in 800 mL of concentrated acetic acid, and 5.0 g of 10% palladium carbon catalyst was added. The reaction mixture was hydrogenated in a hydrogen atmosphere at room temperature for 2.5 hr at a reaction temperature of 50 °C and a hydrogen pressure of 50 psi. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated to dryness. The residue was dissolved in 150 mL of tert-butyl methyl ether, filtered again and dried under vacuum at 100 °C. The resulting product was methyl 2-oxoindoline-6-carboxylate in a yield of 28.6 g (98% of the theoretical yield), with a thin layer chromatographic Rf value of 0.4 (silica gel plate, unfolding agent dichloromethane/methanol = 10:1) and a melting point of 208-211 °C. | [References]
[1] Patent: US6762180, 2004, B1. Location in patent: Page column 53
[2] Journal of Medicinal Chemistry, 2009, vol. 52, # 14, p. 4466 - 4480
[3] Journal of Labelled Compounds and Radiopharmaceuticals, 2015, vol. 58, # 7, p. 308 - 312
[4] Patent: US2015/284327, 2015, A1. Location in patent: Paragraph 0181; 0182; 0207; 0208 |
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