Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Glycine ethyl ester, hydrochloride | HCID 2723640 | — |
| Reactant | HCID 10538822 | HCID 10538822 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 70108068 | HCID 70108068 | 82% |
Reaction Steps
4.71 g (18.6 mmol) of 7-benzoyl-5-methoxyindoline are introduced into 75 ml of pyridine, followed by 16.2 g (116 mmol) of ethyl glycinate hydrochloride. The mixture is heated to 110-115° C. with stirring while distilling off the light fractions which form. After 12 hours, the mixture is cooled and 100 ml of a 2.5% solution of sodium carbonate in water and 100 ml of dichloromethane are added. The aqueous phase is separated out and extracted with 100 ml of dichloromethane. The organic phases are combined and washed with water. The solvent is evaporated off and the residue is then purified by flash chromatography on a column of silica, the eluent used being a gradient of acetone in dichloromethane. 4.15 g of purified product in the form of a brown resin are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05972927 |
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| Source dataset | uspto-grants-1999_10 |
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| ORD ID | ord-d470e03fbdbc4695895c049fdcaa78f0 |
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| Source note | uspto-grants-1999_10 |
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