Methyl 2-oxoindole-6-carboxylate Chemical Properties

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)

pka

13.50±0.20(Predicted)

form 

Solid

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

Hazard Note 

Irritant

HS Code 

2933790090

Methyl 2-oxoindole-6-carboxylate Usage And Synthesis

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

Methyl 2-oxoindole-6-carboxylate(14192-26-8)Related Product Information

• Kresoxim-methyl
• Oxindole
• cis-Octahydro-isoindole
• Methyl salicylate
• Tetrahydro-4H-pyran-4-one
• Methyl carbamate
• Methylparaben
• Methyl formate
• Tribenuron methyl
• Sodium L-pyroglutamate
• Methyl indole-6-carboxylate
• Methyl anthranilate
• RESMETHRIN
• Methyl acrylate
• Dehydroepiandrosterone
• Methyl acetate
• Thiophanate-methyl
• 1-(2,6-Dichlorophenyl)-2-hydroindole