HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → 2-oxo-2,3-dihydro-1H-indole-4-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Hexane | HCID 8058 | — |
| Reactant | Dimethyl 2-methoxycarbonyl-6-nitrophenylmalonate | HCID 54355276 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Product | 2-oxo-2,3-dihydro-1H-indole-4-carboxylic acid | HCID 10397329 | 38.1% |
Reaction Steps
Dimethyl 2-methoxycarbonyl-6-nitrophenylmalonate (3.0 g) was refluxed in 50 mL of 6 N hydrochloric acid overnight. The mixture was concentrated to dryness and refluxed for 2 hours with 1.1 g of tin (11) chloride in 20 mL of ethanol. The mixture was filtered through Celite, concentrated and chromatographed on silica gel in ethyl acetate:hexane:acetic acid to give 0.65 g (37% yield) of 4-carboxy-2-oxindole as a while solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06486185B1 |
| Source dataset | uspto-grants-2002_11 |
| ORD ID | ord-d014433bbe484b25a3e907722e224996 |
| Source note | uspto-grants-2002_11 |